Hydroxyphenylacetic acid → Benzeneacetic acid, 4-hydroxy-, methyl ester

Reaction equation

Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:13]O>>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 127Hydroxyphenylacetic acid

HCID 313Hydrochloric Acid

HCID 887Methanol

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Procedure

Hydrogen chloride was bubbled through a solution of (4-hydroxyphenyl) acetic acid (25 g, 0.16 mole) in methanol (100 ml) at room temperature. An exotherm resulted in the solution refluxing for about 10 minutes. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo to afford methyl(4-hydroxyphenyl)acetate as a yellow oil (27.5 g) which crystallised on seeding, m.p. 46-52° C.