Réaction #170993

Équation de réaction

(4-nitrophenoxy)acetic acid

(4-Nitrophenoxy)acetic acid

triethyl-amine

methyl chloroacetate

→

44

Rendement 90.8%

(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester

Rendement 90.8%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 8 hours
2. 2
   FiltrationSolids were filtered off
3. 3
   workup.ADDITIONpoured onto cold 5% sodium bicarbonate solution (4 L)
4. 4
   FiltrationCrude 44 was filtered
5. 5
   Autredried
6. 6
   Autrerecrystallised from chloroform:hexane (1:6)

Mode opératoire

To a mixture of (4-nitrophenoxy)acetic acid 22 (150 g, 761.4 mmol) and triethyl-amine (85 g, 840 mmol) in acetone (750 ml) was added methyl chloroacetate (91.6 g, 844 mmol) drop wise and stirred under reflux for 8 hours. Solids were filtered off and poured onto cold 5% sodium bicarbonate solution (4 L). Crude 44 was filtered, dried and recrystallised from chloroform:hexane (1:6) to get pure 44 (186 g, 90.8%) as a white powder with an m.p. between 88-90° C.

Source