3',4'-Dimethoxycinnamic acid → 3-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.42 g (2.0 mmol) of 3,4-dimethoxycinnamic acid in 50 ml MeOH was added SOCl2 (50 μl) and the mixture was stirred at 60° C. for 5 h. Methanol was taken to dryness and the obtained 3,4-dimethoxycinnamic acid methyl ester was reduced with 1M THF solution of diisobutylaluminum hydride (8.0 mmol) in absolute THF (50 ml) at 20° C. for 1 h. Water was added, the mixture was extracted with EtOAc, dried with MgSO4 and distilled in vacuo (Kugelrohr apparatus (Aldrich), 0.1 mm Hg, T. oven 185–190° C.) giving an off-white solid, yield 0.36 g (92%), m.p. 70–71° C. The product gave the following analytical data:

Provenance & Evidence