Water → 2-[(4-Methylphenyl)amino]acetic acid

Participants

Reaction Steps

A solution of crude p-tolylamino-acetic acid tert-butyl ester (200 mmol) in DCM (600 mL) was cooled to 0° C. and treated with TFA (150 mL). The reaction mixture was allowed to reach RT and stirred for 4 d. Water (200 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (4×200 mL). The aqueous layer was adjusted to pH 8 by addition of saturated NaHCO3 solution and extracted with ethyl acetate (4×200 mL). The combined organic layers were dried with Na2SO4 and the solvents were removed in vacuo to give the crude acid (18 g) which was used in the next step without further purification.

Provenance & Evidence