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

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Reaction Steps

A solution of lithium aluminum hydride (0.1 mol) in THF (100 ml) was added dropwise to a stirred suspension of 3,4-dimethoxycinnamic acid (41.6 g, 0.2 mol) in THF (150 ml) at room temperature. After the addition, the mixture was stirred for 2 hous, and the solution was evaporated in vacuo to a residue, which was partitioned between dichloromethane and aqueous sodium hydroxide. The organic layer was washed three times with water, dried, and evaporated to an oil. Crystallization from ethyl acetate-hexane gave 3,4-dimethoxycinnamyl alcohol (24 g, 62%), m.p. 76°-77° C.

Provenance & Evidence