Реакция #2045003

ord-1ddc43538ea3433184e3af311a8b5589

Уравнение реакции

CC(=O)Nc1ccc(O)cc1
Paracetamol
O=C([O-])[O-].[K+].[K+]
K2CO3
CCOC(=O)CBr
ethyl bromoacetate
CCOC(=O)COc1ccc(NC(C)=O)cc1
13
Выход 80.1%
CCOC(=O)COc1ccc(NC(C)=O)cc1
(4-Acetylamino-phenoxy)-acetic acid ethyl ester
Выход 80.1%

Реагенты

Нет

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураrefluxed for 16 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (5 liter) was added
  4. 4
    ФильтрацияCrude 13 was filtered
  5. 5
    Другоеdried
  6. 6
    Другоеrecrystallised from a mixture of toluene:hexane (1:5)

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08409559B2uspto-grants-2013_04