Reaction #170955

Reaction equation

Ethyl bromoacetate

paracetamol

K2CO3

→

1

Yield 80.1%

(4-Acetylamino-phenoxy)-acetic acid ethyl ester

Yield 80.1%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 16 hours
2. 2
   workup.DISTILLATIONAcetone was distilled
3. 3
   workup.ADDITIONwater (5 L) was added
4. 4
   FiltrationCrude 1 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from a mixture of toluene:hexane (1:5)

Procedure

Ethyl bromoacetate (452 g, 2.7 mol.) was added to a mixture of paracetamol (300 g, 1.984 mol) and anhydrous K2CO3 (1.80 kg, 7.814 mmol) in anhydrous acetone (3 L) and refluxed for 16 hours. Acetone was distilled and water (5 L) was added. Crude 1 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 1 (377 grams, 80%) as a white shining powder. The melting point was found to be 104.2-106.2° C.

Source