Methanol → Methyl 3-Hydroxyphenylacetate

Participants

Reaction Conditions

Reaction Steps

3-hydroxyphenylacetic acid (111 g, 735.84 mmol) was dissolved under argon in 1000 ml methanol and then sulfuric acid (31.5 mL, 588.6 mmol) was added. The brown mixture was heated (70° C.) for 3 hours, at this temperature, and then cooled to room temperature. The mixture was concentrated in a rotary evaporator and then cooled down to 0° C. 250 mL water and 70 g of NaHCO3 were added with stirring, until the pH was approximately 7.250 mL water was added and 500 ml of ethyl acetate was added. Stirring was pursued for 20 minutes. The organic phase was separated and the aqueous layer extracted with 250 mL ethyl acetate. Drying over magnesium sulfate and concentration in a rotatory evaporator left a brownish oil (118 g, 97%) that was dried at the pump. MS: m/e=165 (M−H+).

Provenance & Evidence