Reaction #2045015

Reaction equation

4-aminophenol

sodium bicarbonate

benzyloxy acetyl chloride

→

26

Yield 48.9%

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

Yield 48.9%

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe solids were filtered off
2. 2
   workup.ADDITIONcold water (500 ml) was added
3. 3
   ExtractionCrude 26 was extracted into chloroform
4. 4
   Washwashed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml)
5. 5
   Dryingdried over sodium sulphate
6. 6
   workup.DISTILLATIONdistilled
7. 7
   OtherThe crude 26 was purified by column chromatography on silica gel

Procedure

To mixture of 4-aminophenol (20 g, 183.2 mmol) and sodium bicarbonate (17 grams, 202 mmol) in acetone (150 ml) at 0° C. was added benzyloxy acetyl chloride (40 g, 216.8 mmol) drop wise, followed by stirring at room temperature for 20 hours. The solids were filtered off, and cold water (500 ml) was added. Crude 26 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml), dried over sodium sulphate and distilled. The crude 26 was purified by column chromatography on silica gel using chloroform as eluant to get pure 26 (23 g, 48.9%) as a light orange syrup.

Source