Reaction #2045020

Reaction equation

4-Nitro phenol

K2CO3

methyl chloroacetate

→

31

Yield 72.5%

Methyl(4-Nitro phenoxy)acetate

Yield 72.5%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 12 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) added
4. 4
   FiltrationCrude 31 was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Procedure

To a mixture of 4-Nitro phenol (100 g, 719 mmol) and anhydrous K2CO3 (400 g, 2.894 moles) in anhydrous acetone (950 ml) was added methyl chloroacetate (114 g, 1.050 moles) and refluxed for 12 hours. Acetone was distilled off and water (1500 ml) added. Crude 31 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 31 (110 g, 72.5%) as a white fluffy powder. M.p: 97-98.4° C.

Source