1,2-Dimethoxyethane → Ethyl 2-nitro-4-benzoylphenylacetate

HRID 414412

Reaction equation

HRID 414412 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([OH:21])=[O:20])([O-:3])=[O:2].CO[CH2:24][CH2:25]OC.C(N(CC)CC)C.C(OC(Cl)=O)C>[Cl-].[Na+].O.C(OCC)C.C(O)C>[N+:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH2:24][CH3:25])=[O:20])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 137705362-Nitro-4-benzoylphenylacetic acid

Product 1

HCID 13770535Ethyl 2-nitro-4-benzoylphenylacetateYield 94%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
10 °C

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.

Workup

  1. customthe reaction
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oil, which
  5. customto crystallize

Sources & evidence

ORD record
ord-24e2dd8278be4d16b4c555d57de40619
Source dataset
uspto-grants-1988_12
Patent number
US04791129

Linked notes

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