Methanol → Methyl 3-Hydroxyphenylacetate

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (17 mL, 0.64 mol) was added dropwise to methanol at 0° C. After the completion of the addition, the reaction mixture was stirred at 0° C. for 10 min., and then 3-hydroxyphenylacetic acid (25 g, 0.16 mol) was added. The resulting reaction mixture was stirred at room temperature for 2 h. Volatiles were removed and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with H2O, NaHCO3, and NaCl (sat.) and dried over Na2SO4. The crude product was purified on a silica gel column with 20% EtOAc in hexane to give methyl 3-hydroxyphenylacetate as a colorless oil (25 g, 94% yield).

Provenance & Evidence