Hydrochloric Acid → Methyl 3-allyl-4-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixed solution of methyl 4-(2-propen-1-yl)oxybenzoate (19.17 g, 0.10 mol) and N,N-dimethylaniline (40 mL) was heated under reflux at 210° C. for 18 hours. Dilute hydrochloric acid (1 mol/L) was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 12.26 g of the title compound (yield: 64%) as a colorless powder.

Provenance & Evidence