3,4,5-Trimethoxybenzylalcohol

50g (280 mmol) 3,4,5-trimethoxybenzaldehyde was dissolved in 600mL methanol at 0°C (ice-bath) under stirring. Then 10g NaBH₄ was added in 3 portions and the reaction was left overnight with continued stirring.

The next day most of the methanol was removed under vacuum (important to get a nice extraction) and the residue diluted with water (500mL) and made acid with 37% HCl. The aqueous solution was extracted with 4x100mL CH₂Cl₂, the organic phases was combined, dried and concentrated under vacuum.

Yield: 47.2g (93%) 3,4,5-Trimethoxybenzylalcohol,
TLC R_f 0.27 (40% EtOAc in Heptane)

3,4,5-Trimethoxybenzylbromide

47.2g (240 mmol) 3,4,5-trimethoxybenzaldehyde was dissolved into 1L ether at 0°C (ice-bath) under stirring. Then 25g (100 mmol) PBr₃ was added over 30min, the ice-bath removed and the reaction left to stir for 60 min. After that the mixture was poured into 300mL water, the organic phase was separated, the aqueous phase extracted with 2x100mL ether, the ether phases combined, washed with 2x50mL water, dried and concentrated (under vacuum).

Yield: 55g (88%) 3,4,5-Trimethoxybenzylbromide,
TLC R_f 0.63 (50% EtOAc in Heptane)

3,4,5-Trimethoxybenzyl Cyanide

50g (190 mmol) 3,4,5-trimethoxybenzylbromide was dissolved into 600mL DMF under stirring at 0°C (ice-bath), then 20g NaCN vas added and the ice-bath removed. After 1 hour the mixture was poured into 2L water, the water was extracted with 4x100mL CH₂Cl₂. The organic phases was combined, washed with 2x100mL water, dried and concentrated.

Yield: 36g (90%) 3,4,5-Trimethoxybenzyl cyanide,
TLC R_f 0.45 (50% EtOAc in heptane)

3,4,5-Trimethoxyphenethylamine (Mescaline)

15g (70 mmol) 3,4,5-trimethoxybenzylcyanide was dissolved in 100mL ethanol, 10mL 37% hydrochloric acid and 100mg 10% Pd/C was added and the mixture was hydrogenated at 5.5 bar for 12 hours, then the mixture was filtered, most of the ethanol was evaporated off, then the mixture was dissolved into 200mL water, extracted with 50mL ether (to remove unreacted starting material etc.), made basic with NaOH, extracted with 3x40mL CH₂Cl₂ and the pooled organic phases was combined, dried and evaporated.

Yield: 13.7g Mescaline freebase.