Reaction #2045016

Reaction equation

2-Benzyloxy-N-(4-hydroxy-phenyl)-acetamide

→

27

Yield 34.2%

2-Hydroxy-N-(4-hydroxy-phenyl)-acetamide

Yield 34.2%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   workup.DISTILLATIONthe methanol was distilled off
3. 3
   OtherThe crude 27 was recrystallized from a mixture of chloroform:methanol (1:5)

Procedure

2-Benzyloxy-N-(4-hydroxy-phenyl)-acetamide 26 (18 g, 70 mmol) was dissolved in methanol (100 ml) in a pressure vessel, palladium on carbon (5%, 8 g) was added and the mixture stirred under an atmosphere of hydrogen (4 Kg) for 8 hours. The catalyst was removed by filtration and the methanol was distilled off. The crude 27 was recrystallized from a mixture of chloroform:methanol (1:5) to get pure 27 (4 grams, 34.2%) as a white shining powder.

Source