Réaction #170955

Équation de réaction

Ethyl bromoacetate

paracetamol

K2CO3

→

1

Rendement 80.1%

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

Rendement 80.1%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed 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
   Autredried
6. 6
   Autrerecrystallised from a mixture of toluene:hexane (1:5)

Mode opératoire

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