Citric Acid → 2-Methylphenethyl alcohol

Participants

Reaction Conditions

Reaction Steps

1250 Grams of isochroman having the structure: ##STR64## 25 grams of 5% palladium-on-carbon and 12.5 grams of citric acid are placed in a 4-liter autoclave. The autoclave is sealed, heated to 150° C. and pressurized with hydrogen at 200 psig. After five hours, 12.5 grams of additional citric acid is added to the autoclave and the autoclave is resealed. The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours. At the end of this additional three hour period, the autoclave is opened, the contents filtered and the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions:

Provenance & Evidence