Reaction #4569

Reaction equation

2-nitro-4-benzoylphenylacetic acid

triethylamine

ethylchloroformate

1,2-dimethoxyethane

→

ethyl 2-nitro-4-benzoylphenylacetate

Yield 94.0%

Solvents

brine

diethyl ether

Ethanol

Conditions

Workup

1. 1
   Otherthe reaction
2. 2
   OtherThe organic phase was separated
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Concentrationconcentrated to an oil, which
5. 5
   Otherto crystallize

Procedure

To a solution of 13.8 g. (48.4 mmoles) of 2-nitro-4-benzoylphenylacetic acid in 150 ml. of 1,2-dimethoxyethane at 15° C. was added 5.87 g. (58.1 mmole) of triethylamine. After 5 minutes 5.75 g. (53.2 mmoles) of ethylchloroformate was added and the reaction mixture allowed to stir at 10° C. for 15 minutes. Ethanol (15 ml.) was added and the reaction subsequently was added to a mixture of diethyl ether and a saturated brine solution. The organic phase was separated, dried over magnesium sulfate and concentrated to an oil, which was induced to crystallize, 14.3 g. (94% yield), m.p. 61°-62° C.

Source