Reaction #725898

Reaction equation

Benzyloxyacetic acid 4-acetylamino-phenyl ester

Benzyloxy-acetic acid 4-acetylamino-phenyl ester

→

25

Yield 57.4%

Hydroxy-acetic acid 4-acetylamino-phenyl ester

Yield 57.4%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   workup.DISTILLATIONthe methanol was then distilled off
3. 3
   OtherThe crude 25 was recrystallized from mixture of chloroform:methanol (1:4)

Procedure

Benzyloxyacetic acid 4-acetylamino-phenyl ester 24 (15 g, 50 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (5%, 8 grams) added and the mixture stirred under an atmosphere of hydrogen (3 Kg) for 20 hours. The catalyst was removed by filtration and the methanol was then distilled off. The crude 25 was recrystallized from mixture of chloroform:methanol (1:4) to get pure 25 (6 g, 57.2%) as a white powder. M.p: 144-146° C.

Source