Nitrostyrene Synthesis - Reference Collection

Introduction

What follows is a compilation of omega-nitrostyrene syntheses taken from Houben-Weyl. There are 4 sections:

Benzaldehydes with Nitromethane
Benzaldehydes with Nitroethane
Benzaldehydes with Nitropropane
Benzaldehydes with Nitrobutane

The "Parts" subdivision of the section agree with different pages from Houben-Weyl.
Hence, many references are mentioned several times.

Reference:

Houben-Weyl, Methoden der organischen Chemie. Band X/1, Stickstoffverbindungen I, Teil I, pp 342-357

Used abreviations for references:
A	Liebigs Annalen der Chemie
Am Soc	Journal of the American Chemical Society
Ang Ch	Angewandte Chemie
Ar	Archiv der Pharmazie
B	Berichte der Deutschen Chemischen Gesellschaft
Bl	Bulletin de la Societe Chimique de France
C	Chemisches Zentralblatt
CA	Chemical Abstracts
Canad J Res	Canadian Journal of Research
CR	Comptes Rondus Hebdomadaires des Seances de l'Academie des Sciences
Doklady Akad SSSR	Doklady Akademii Nauk SSSR (Russian)
Helv	Helvetica Chimica Acta
J agr chem Soc Japan	Journal of the agricultural and chemical Society of Japan
J Indian chem Soc	Journal of the Indian Chemical Society
J Org Chem	Journal of Organic Chemistry
J Pharm Soc Japan	Journal of the Pharmaceutical Society of Japan
J pr	Journal fuer Praktische Chemie
M	Monatshefte fuer Chemie
Org Synth Coll	Organic Synthesis Collection
R	Recueil des Travaux Chimiques des Pays-Bas
S P In phys chem Res	Scientific Papers of the Institute of Physical and Chemical Research. Tokyo
Soc	Journal of the Chemical Society. London
Z obsc Chim	Zurnal Obscej Chimii (Russian) (aka Journal of General Chemistry)
Z Org Chim	Journal of Organic Chemistry (Russian)

Benzaldehydes + Nitromethane Condensations

Format: Precursor, Yield(%), reference(s)

Part 1

benzaldehyde, 80-83, [1-7]
4-methylbenzaldehyde, *, [7,8]
2-fluorbenzaldehyde, 70-75, [9,10]
2-chlorobenzaldehyde, *, [7,11,12]
3-chlorobenzaldehyde, 34, [7,12]
4-chlorobenzaldehyde, *, [7,12,13]
2-bromobenzaldehyde, 50, [12-14]
3-bromobenzaldehyde, *, [15]
4-bromobenzaldehyde, *, [11]
2-iodobenzaldehyde, 65-70, [16]
2-nitrobenzaldehyde, *, [7,13,17,18]
3-nitrobenzaldehyde, 76, [3,7,11,13,19,20]
4-nitrobenzaldehyde, *, [3,5,7,13]
3-cyanobenzaldehyde, 42, [21]
3-thiocyanatbenzaldehyde, 80, [22]
4-thiocyanatbenzaldehyde, 70, [22]
2-carboxybenzaldehyde, *,[7,23]

[1] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol I, 413 (1932)
[2] E Knoevenagel, L Walter, B 37, 4502 (1904)
[3] J Thiele, B 32, 1293 (1899)
[4] M Holleman, R 23, 283 (1904)
[5] J Thiele, S Haeckel, A 325, 1 (1902)
[6] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[7] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[8] DE Worral, Am Soc 60, 2841 (1938)
[9] AV Topchiev, VP Alaniya, MF Vagin, Doklady Akad SSSR 151, 114 (1963) [CA 59.10245 (1963)]
[10] DE Worral, HT Wolosinki, Am Soc 62, 2449 (1940)
[11] DE Worral, Am Soc 56, 1556 (1934)
[12] N Campbell, W Anderson, J Gilmore, Soc (1940) 446
[13] FGP Remfry, Soc 99, 282 (1911)
[14] DE Worrall, J Finkel, Am Soc 61, 2969 (1939)
[15] H Kondo, S Ishiwata, B 64, 1533 (1931)
[16] DE Worrall, F Benington, Am Soc 62, 493 (1940)
[17] L Bouveault, A Wahl, C R 135, 41 (1902); C (1902) II, 449
[18] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[19] K H Slotta, G Szyszka, B 68, 184 (1935)
[20] AK De, J Indian Chem Soc 5, 29 (1928); C (1928) I, 2393
[21] KH Slotta, R Kethur, B 71, 59 (1938)
[22] JP19155 (1964) [CA 62.7864 (1965)]
[23] T Hashimoto, S Nagase, J Pharm Soc Japan 80, 1637 (1960) [CA 55.7415 (1961)]

Part 2

2-hydroxybenzaldehyde, 34, [1-3]
3-hydroxybenzaldehyde, 66, [2,3]
4-hydroxybenzaldehyde, 60, [1,2,4]
4-acetoxybenzaldehyde, 11, [2,3]
4-benzyloxybenzaldehyde, *, [5]
3-benzyloxybenzaldehyde, *, [6]
4-benzoylbenzaldehyde, *, [2,5]
2-methoxybenzaldehyde, 82, [4]
3-methoxybenzaldehyde, *, [7]
4-methoxybenzaldehyde, 86, [1,4,8-15]
2-ethoxybenzaldehyde, 30, [4,16]
4-dimethylaminobenzaldehyde, *, [1,17]
4-diethylaminobenzaldehyde, 70, [16]
4-acetaminobenzaldehyde, 89, [1,16]
4-methylmercaptobenzaldehyde, *, [18]
4-ethylmercaptobenzaldehyde, *, [18]
4-allylmercaptobenzaldehyde, *, [18]
4-propyn-1-ylmercaptobenzaldehyde, *, [18]
4-aminosulfonbenzaldehyde, *, [19]
2,4-dichlorobenzaldehyde, 62, [1,20]
2,6-dichlorobenzaldehyde, 74, [16]
3,4-dichlorobenzaldehyde, *, [1]

[1] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[2] FGP Remfry, Soc 99, 282 (1911)
[3] G Hahn, K Stiehl, B 71, 2154 (1938)
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] KW Rosenmund, B 46, 1034 (1913)
[6] H Kondo, S Ishiwata, B 64, 1533 (1931)
[7] JB Shoesmith, RJ Connor, Soc (1927) 2230
[8] DE Worrall, Am Soc 56, 1556 (1934)
[9] L Bouveault, A Wahl, C R 135, 41 (1902); C (1902) II, 449
[10] E Knoevenagel, L Walter, B 37, 4502 (1904)
[11] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[12] KW Rosenmund, B 42, 4778 (1909)
[13] T Kondo, Y Shinozaki, J Pharm Soc Japan 49, 267 (1929) [CA 24.5294 (1930)]
[14] MPJM Jansen, R 50, 291 (1931)
[15] DE161171
[16] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[17] JR Merchant, SR Agrawal, J Indian chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[18] JP28323 [CA 62.11739 (1965)]
[19] JP467 [CA 59.11380 (1963)]
[20] MB Neher, EW Goldberg, RW Fairchild, J Org Chem 26, 5220 (1961)

Part 3

2,3,6-trichlorobenzaldehyde, *, [1]
4-chloro-3-nitrobenzaldehyde, *, [2]
2-chloro-3-ethoxybenzaldehyde, 76, [3]
3-bromo-4-methoxybenzaldehyde, *, [4]
4-methoxy-3-chloromethylbenzaldehyde, *, [5]
3,5-dichloro-4-hydroxybenzaldehyde, 50, [6]
2,6-dichloro-3-methoxybenzaldehyde, 70, [7]
4-chloro-3-hydroxybenzaldehyde, 60, [2]
2-chloro-3-hydroxybenzaldehyde, 70, [7]
2-chloro-3-methoxybenzaldehyde, 80, [7]
4-chloro-3-rhodanbenzaldehyde, 50, [2]
5-chloro-2-hydroxybenzaldehyde, 12, [8]
3,4-dihydroxybenzaldehyde, *, [5]
2-hydroxy-4-methoxybenzaldehyde, *, [9]
2-hydroxy-3-methoxybenzaldehyde, 78, [10,11]
3-hydroxy-4-methoxybenzaldehyde, 63, [12,13]

[1] US3112346
[2] JP 28318 [CA 62.11736 (1965)]
[3] GS Sidhu, PB Sattur, SJ Hasan. J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[4] M Kondo, S Ishiwata, B 64, 1533 (1931)
[5] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[6] JP26960 [CA 62.14569 (1965)]
[7] GS Sidhu, PB Sattur, SJ Hasan. J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)] (sic)
[8] O Schales, HA Graeffe, Am Soc 74, 4486 (1952)
[9] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[10] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[11] VG Voronin, GD Kulikovskaya, LD Magda, Z Org Chim 1, 719 (1965) [CA 63.5546 (1965)]
[12] G Hahn, K Stiehl, B 71, 2154 (1938)
[13] G Hahn, F Rumpf, B 71, 2141 (1938)

Part 4

3-hydroxy-4-ethoxybenzaldehyde, 18, [1]
4-hydroxy-3-methoxybenzaldehyde (vanillin), 95, [2-5]
4-hydroxy-3-ethoxybenzaldehyde, 75, [4]
2,3-dimethoxybenzaldehyde, 60, [4]
2,3-diethoxybenzaldehyde, 59, [1]
2,4-dimethoxybenzaldehyde, *, [3,13]
2,4-diethoxybenzaldehyde, *, [14]
3,4-dimethoxybenzaldehyde, 80, [4,15-19]
2,5-dimethoxybenzaldehyde, *, [20,21]
3,4-methylenedioxybenzaldehyde (piperonal), 75, [2,7,15,19,22-26]
3-methoxy-4-benzyloxybenzaldehyde, 97, [27-31]
4-methoxy-3-benzyloxybenzaldehyde, 88, [16,30]

[1] A Dornow, G Petsch, Ar 284, 153 (1951)
[2] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[3] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] G Hahn, K Stiehl, B 71, 2154 (1938)
[6] DE Worrall, Am Soc 56, 1556 (1934)
[7] E Knoevenagel, L Walter, B 37, 4502 (1904)
[8] KW Rosenmund, B 46, 1034 (1913)
[9] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[10] ON Tolkachev, VG Voronin, NA Preobrazhenskii, Z obsc Chim 28, 3320 (1958) [CA 53.14029 (1959)]
[11] DE247817
[12] SP Makarow, J pr 141, 77 (1934)
[13] C Mannich, M Falber, Ar 267, 601 (1929); C (1930) I, 77
[14] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[15] KH Slotta, G Haberland, Ang Ch 46, 766 (1933)
[16] R Robinson, S Sugasawa, Soc (1931) 3163
[17] H Kondo, T Kondo, J Pharm Soc Japan 48, 56 (1927); C (928) II, 55
[18] G Barger, J Eisenbrand, L Eisenbrand, E Schlittler, B 66, 450 (1933)
[19] KW Rosenmund, B 43, 3412 (1910)
[20] FGP Remfry, Soc 99, 282 (1911)
[21] S Sugasawa, H Shigehara, B 74, 459 (1941)
[22] L Bouveault, A Wahl, CR 135, 41 (1902); C (1902) II, 449
[23] P Medinger, M 27, 238 (1906)
[24] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[25] Y Tanaka, T Midzuno, J Pharm Soc Japan 49, 47 (1929); C (1929) I, 2978
[26] PW Neber, A Burgard, W Thier, A 526, 277 (1936)
[27] NA Lange, WE Hambourger, Am Soc 53, 3865 (1936)
[28] M Tomita, H Watanabe, J Pharm Soc Japan 58, 223 (1938); C (1939) I, 1978
[29] S Kobayashi, S P In phys chem Res 6, 149 (1927); C (1928) I, 1026
[30] E Spaeth, A Orechoff, F Kuffner, B 67, 1214 (1934)
[31] H Kondo e.a., Itsuu Kenkyusho Nempo 9, 1 (1958) [CA 54.1399 (1960)]

Part 5

4-methoxy-2-ethoxybenzaldehyde, *, [1,2]
3-methoxy-4-ethoxybenzaldehyde, 85, [3-7]
4-methoxy-3-ethoxybenzaldehyde, 64, [3,6,8]
3-methoxy-2-propyloxybenzaldehyde, 27, [9]
3-methoxy-2-isopropyloxybenzaldehyde, 29, [9]
3-methoxy-2-butyloxybenzaldehyde, 20, [9]
3-methoxy-2-pentyloxybenzaldehyde, 57, [9]
3-methoxy-2-(3-methylbutyloxy)-benzaldehyde, 43, [9]
3-ethoxy-2-isopropyloxybenzaldehyde, 52, [9]
3-ethoxy-2-butyloxybenzaldehyde, 66, [9]
3-ethoxy-2-pentyloxybenzaldehyde, 47, [9]
3,4-dibenzyloxybenzaldehyde, *, [8]
3-nitro-2-hydroxybenzaldehyde, *, [10]
3-nitro-4-methoxybenzaldehyde, 74, [10-12]
3-nitro-4-hydroxybenzaldehyde, *, [12]
2-nitro-3-methoxybenzaldehyde, 85, [13]
2-nitro-4-methoxybenzaldehyde, 70, [13]
2-nitro-5-methoxybenzaldehyde, 80, [13]
2-nitro-5-acetoxybenzaldehyde, quant, [14]

[1] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[2] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[3] E Spaeth, A Dobrowsky, B 58, 1274 (1934)
[4] T Kondo, K Shinozaki, K Ishi, J Pharm Soc Japan 48, 169 (1928); C (1929) I, 1112
[5] K Sawai, J Pharm Soc Japan 49, 260 (1929); C (1929) I, 2749
[6] A Dornow, G Petsch, Ar 284, 153 (1951)
[7] KW Bentley, SF Dyke, J Org Chem 22, 429 (1957)
[8] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[9] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[10] FGP Remfry, Soc 99, 282 (1911)
[11] KH Slotta, G Szyszka, B 68, 184 (1935)
[12] JP26960 [CA 62.14569 (1965)]
[13] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[14] RJS Beer, K Clarke, HG Khorana, A Robertson, Soc (1948) 1605

Part 6

6-nitro-2-acetoxybenzaldehyde, quant, [1]
2-nitro-4-methylbenzaldehyde, 65, [2]
4-methoxy-3-rhodanbenzaldehyde, *, [3]
2-iodo-3-methoxybenzaldehyde, 75, [2]
2-hydroxy-3-carboxybenzaldehyde, *, [4]
5-bromo-2,3-dimethoxybenzaldehyde, 90, [5,6]
3,5-dibromo-4-hydroxybenzaldehyde, *, [3]
4,5-dimethoxy-2-methylbenzaldehyde, *, [7]
4,5-dimethoxy-2-ethylbenzaldehyde, *, [7]
2,4-dimethoxy-3-methylbenzaldehyde, *, [7]
2,4-dimethoxy-3-ethylbenzaldehyde, *, [7]
4,6-dimethoxy-2-methylbenzaldehyde, *, [5]
2,4-diethoxy-3-methylbenzaldehyde, *, [7]
4,6-diethoxy-2-methylbenzaldehyde, *, [5]
2-methoxy-3,5-dimethylbenzaldehyde, *, [7]
2-methoxy-4,5-dimethylbenzaldehyde, *, [7]
2,4-dimethoxy-3-benzylbenzaldehyde, *, [7]
2,4-diethoxy-3-benzylbenzaldehyde, *, [7]
4-methoxy-6-ethoxy-2-methylbenzaldehyde, *, [5]
4-methoxy-2,6-dimethylbenzaldehyde, *, [5]
4-ethoxy-2,6-dimethylbenzaldehyde, *, [5]
6-methoxy-2,4-dimethylbenzaldehyde, *, [5]

[1] RJS Beer, K Clarke, HG Khorona, A Robertson, Soc (1948) 1695
[2] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[3] JP26960 [CA 62.14569 (1965)]
[4] FGP Remfry, Soc 99, 282 (1911)
[5] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[6] VG Voronin, GD Kulikovskaya, LD Magda, Z Org Chim 1,719 (1965) [CA 63.5546 (1965)]
[7] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]

Part 7

6-ethoxy-2,4-dimethylbenzaldehyde, *, [1]
4-hydroxy-3,5-dimethoxybenzaldehyde, 97, [2,3]
2,3,4-trimethoxybenzaldehyde, 73, [4]
2,3,5-trimethoxybenzaldehyde, *, [1]
2,4,5-trimethoxybenzaldehyde, *, [5]
3,4,5-trimethoxybenzaldehyde, 78, [2,4,6,7]
3,4,5-triethoxybenzaldehyde, 55, [4]
3,5-dimethoxy-4-ethoxybenzaldehyde, 65, [3]
5-bromo-2-hydroxy-3-methoxybenzaldehyde, *, [8]
5-iodo-2-hydroxy-3-methoxybenzaldehyde, 26, [8]
5-bromo-4-hydroxy-3-methoxybenzaldehyde, *, [9,10]
2-bromo-3,4-dimethoxybenzaldehyde, 77, [11]
5-bromo-3,4-dimethoxybenzaldehyde, 50, [12]
" , 80, [13] (different MP)
5-iodo-2,3-dimethoxybenzaldehyde, *, [8]
5-nitro-3,4-dimethoxybenzaldehyde, *, [7]
5-nitro-2,4-dimethoxybenzaldehyde, *, [14]
4-methoxy-2,3,6-trimethylbenzaldehyde, *, [15]
2,5-dimethoxy-3,4-methylenedioxybenzaldehyde, *, [16]

[1] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[2] F Mauthner, J pr [2] 92, 194 (1915)
[3] F Benington, RD Morin, LC Clarke, Am Soc 76, 5555 (1954)
[4] KH Slotta, G Szyszka, J pr [2] 137, 339 (1933)
[5] MPJM Jansen, R 50, 291 (1931)
[6] E Spaeth, M 40, 129 (1919)
[7] KH Slotta, G Szyszka, B 98, 184 (1935)
[8] E Profft, M Pannach, Ar 299, 633 (1966)
[9] ON Tolkachev, VG Voronin, NA Preobrazhenskii, Z Obsc Chim 28, 3320 (1958) [CA 53.14029 (1959)]
[10] SP Makarow, J pr 141, 77 (1934)
[11] K Bessho, Chem Pharm Bull (Tokyo) 11, 1491 (1963)
[12] M Tomita, H Watanabe, J Pharm Soc Japan 58, 223 (1938)
[13] H Kondo e.a, Itsuu Kenkyusho Nempo 9, 1 (1958) [CA 54.1399 (1960)]
[14] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[15] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[16] Mannich, M Falber, Ar 267, 601 (1929); C (1930) I, 77

Benzaldehydes + Nitroethane Condensations

Format: Precursor, Yield(%), reference(s)

Part 2

benzaldehyde, 85, [5-10]
4-methylbenzaldehyde, 38, [10]
4-trifluoromethylbenzaldehyde, 55, [11]
2-chlorobenzaldehyde, 66, [10,12]
3-chlorobenzaldehyde, 53, [10]
4-chlorobenzaldehyde, 76, [10]
4-hydroxybenzaldehyde, 35, [9,10,12]
2-methoxybenzaldehyde, 91, [13]
3-methoxybenzaldehyde, 54, [12]
4-methoxybenzaldehyde, 60, [6,7,9,10,12,14]
2-ethoxybenzaldehyde, 73, [12]

[5] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol 1, 405 (1932)
[6] E Knoevenagel, L Walter, B 37, 4502 (1904)
[7] GA Alles, Am Soc 54, 271 (1932)
[8] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[9] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[10] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)]
[11] GB870541; US3117160
[12] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[13] GB671240
[14] FW Hoover, HB Hass, J Org Chem 12, 501 (1947)

Part 2

2-nitrobenzaldehyde, 46, [1]
" , 62, [1] (different MP)
3-nitrobenzaldehyde, 12, [1]
4-nitrobenzaldehyde, 55, [1,2]
4-aminosulfonbenzaldehyde, *, [3]
4-diethylaminobenzaldehyde, 18, [2]
4-acetaminobenzaldehyde, 30, [2]
2,4-dichlorobenzaldehyde, 73, [2]
3,4-dichlorobenzaldehyde, 52, [2]
4-methoxy-3-chloromethylbenzaldehyde, 78, [1]
2-hydroxy-3-methoxybenzaldehyde, 45, [2,4]
4-hydroxy-3-methoxybenzaldehyde, 72, [1,4-6]
3-methoxy-4-benzoyloxybenzaldehyde, 72, [5]
4-hydroxy-3-ethoxybenzaldehyde, 50, [4]
2,3-dimethoxybenzaldehyde, 79, [2,4]
3,4-dimethoxybenzaldehyde, 35, [4,7]
3,4-methylenedioxybenzaldehyde (piperonal), 80, [1,8]
3-methoxy-2-propyloxybenzaldehyde, 71, [9]

[1] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)]
[2] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[3] JP17017 [CA 60.13184 (1964)]
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[6] LV Fennoy, J Org Chem 26, 4696 (1961)
[7] GA Alles, Am Soc 54, 271 (1932)
[8] E Knoevenagel, L Walter, B 37, 4502 (1904)
[9] E Profft, Arzneimittel-Forsch 9, 157 (1959)

Part 3

3-methoxy-2-isopropoxybenzaldehyde, 67, [1]
3-methoxy-2-butyloxybenzaldehyde, 53, [1]
3-methoxy-2-(2-methylpropyloxy)-benzaldehyde, 57, [1]
3-methoxy-2-pentyloxybenzaldehyde, 48, [1]
3-methoxy-2-(3-methylbutyloxy)-benzaldehyde, 48, [1]
3-methoxy-2-hexyloxybenzaldehyde, 64, [1]
3-methoxy-2-octyloxybenzaldehyde, 63, [1]
2-methoxy-3-ethoxybenzaldehyde, 31, [1]
3-ethoxy-2-propyloxybenzaldehyde, 51, [1]
3-ethoxy-2-isopropyloxybenzaldehyde, 62, [1]
3-ethoxy-2-butyloxybenzaldehyde, 60, [1]
3-ethoxy-2-(2-methylpropyloxy)-benzaldehyde, 62, [1]
3-ethoxy-2-pentyloxybenzaldehyde, 46, [1]
3-ethoxy-2-(3-methylbutyloxy)-benzaldehyde, 57, [1]
3-ethoxy-2-octyloxybenzaldehyde, 69, [1]
3-ethoxy-2-dodecyloxybenzaldehyde, 77, [1]
2-nitro-5-acetoxybenzaldehyde, *, [2]
5-bromo-2-hydroxy-3-methoxybenzaldehyde, *, [3]

[1] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[2] RJS Beer, K Clark, HG Khorana, A Robertson, Soc (1948), 1605
[3] E Profft, M Pannach, Ar 299, 633 (1966)

Benzaldehydes + Nitropropane Condensations

Format: Precursor, Yield(%), reference(s)

Part 1

Benzaldehyde, 70, [1-3]
2-Chlorobenzaldehyde, 68, [3]
3-Chlorobenzaldehyde, 36, [3]
4-Chlorobenzaldehyde, 7, [3]
3-Nitrobenzaldehyde, 62, [3]
4-Nitrobenzaldehyde, 10, [3]
4-Methylbenzaldehyde, 34, [3]
4-Hydroxybenzaldehyde, 22, [3]
4-Methoxybenzaldehyde, 90, [1,3]
4-Hydroxy-3-methoxybenzaldehyde, 54, [3-5]
3,4-Methylenedioxybenzaldehyde (Piperonal), 48, [3]
3-Methoxy-4-benzoyloxybenzaldehyde, *, [4]
3-Methoxy-2-propyloxybenzaldehyde, 50, [6]
3-Methoxy-2-isopropyloxybenzaldehyde, 21, [6]
3-Methoxy-2-butyloxybenzaldehyde, 36, [6]
3-Methoxy-2-(2-methylpropyloxy)-benzaldehyde, 34, [6]
3-Methoxy-2-pentyloxybenzaldehyde, 26, [6]

[1] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[2] PC Ferreira, LA de Pontes, Anais fac farm e odontol univ Sao Paulo 12, 1 (1954) [CA 50.10667 (1956)]
[3] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]
[4] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[5] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[6] E Profft, Arzneimittel-Forsch 9, 157 (1959)

Part 2

3-Methoxy-2-(3-methylbutyloxy)-benzaldehyde, 39, [1]
3-Methoxy-2-nonyloxybenzaldehyde, 36, [1]
3-Ethoxy-2-isopropyloxybenzaldehyde, 14, [1]
3-Ethoxy-2-hexyloxybenzaldehyde, 37, [1]
3-Ethoxy-2-nonyloxybenzaldehyde, 31, [1]
[...]
3-Nitro-4-hydroxybenzaldehyde, 50, [5]
3-Nitro-4-methoxybenzaldehyde, 40, [5]
3,5-Dichloro-4-hydroxybenzaldehyde, 40, [5]

[1] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[5] JP26960 [CA 62.14569 (1965)]

Benzaldehydes + Nitrobutane Condensations

Format: Precursor, Yield (%), Reference(s)

Part 1

benzaldehyde, 65-70, [2,6]
4-chlorobenzaldehyde, 86, [6]
3-chlorobenzaldehyde, 52, [6]
2-chlorobenzaldehyde, 77, [6]
4-nitrobenzaldehyde, 47, [6]
3-nitrobenzaldehyde, 31, [6]

[2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[6] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]

Part 2

2-nitrobenzaldehyde, 47, [1]
4-methylbenzaldehyde, 52, [1]
4-methoxybenzaldehyde, 90, [1,2]
4-hydroxybenzaldehyde, 22, [1]
4-hydroxy-3-methoxybenzaldehyde, 23, [1]
3,4-methylenedioxybenzaldehyde (piperonal), 36, [1]
3-thiocyanobenzaldehyde, 40, [3]
4-thiocyanobenzaldehyde, 39, [3]

[1] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]
[2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[3] JP19155 [CA 62.7684 (1965)]

beta-Nitrostyrene Synthesis - Reference Collection

Henry Condensation of Benzaldehydes with Primary Nitroalkanes

Introduction

Benzaldehydes + Nitromethane Condensations

Part 1

Part 2

Part 3

Part 4

Part 5

Part 6

Part 7

Benzaldehydes + Nitroethane Condensations

Part 2

Part 2

Part 3

Benzaldehydes + Nitropropane Condensations

Part 1

Part 2

Benzaldehydes + Nitrobutane Condensations

Part 1

Part 2