2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

Participants

Reaction Steps

2-Hydroxy-4-methylbenzoic acid was reacted with K2CO3 and dimethyl sulfate to give methyl 2-methoxy-4-methybenzoate (boiling point at 0.7 mm=100° C.). Hydrolysis with 2N sodium hydroxide solution provided 2-methoxy-4-methylbenzoic acid (melting point 103°-104° C.). Bromination to give the 4-bromomethyl compound (melting point 123°-125° C.) and reaction with potassium cyanide provided the 4-cyanomethyl compound (melting point 105°-107° C., from toluene), the catalytic hydrogenation of which with Ra--Ni and reaction with ethanolic hydrochloric acid provided the ethyl 4-(2-aminoethyl)-2-methoxybenzoate hydrochloride (melting point 86°-88° C.).

Provenance & Evidence