Reaction #725887

Reaction equation

Paracetamol

K2CO3

ethyl bromoacetate

→

13

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 off
3. 3
   workup.ADDITIONwater (5 liter) was added
4. 4
   FiltrationCrude 13 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from a mixture of toluene:hexane (1:5)

Procedure

To a mixture of Paracetamol (300 g, 1.984 mol), and anhydrous K2CO3 (1.80 Kg, 7.814 mmol) in anhydrous acetone (3 liters) was added ethyl bromoacetate (452 gr, 2.7 mol) and refluxed for 16 hours. Acetone was distilled off and water (5 liter) was added. Crude 13 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 13 (377 g, 80%) as a white shining powder. The melting point was found to be 104.2-106.2° C.

Source