Ethanol → Ethyl 4-(2-nitrophenyl)-3-oxobutanoate

HRID 1833882Notes

Reaction equation

HRID 1833882 reaction equation
C(OC(=O)C[C:6]([CH2:8][C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])=[O:7])C.[CH2:22]([OH:24])[CH3:23]>>[CH2:22]([O:24][C:6](=[O:7])[CH2:8][C:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])=[O:20])[CH3:23]

Participants

3

Reactant 2

HCID 702EthanolHCID 131710861Ethyl-o-nitrophenylacetylacetoacetate

Product 1

HCID 10857922Ethyl 4-(2-nitrophenyl)-3-oxobutanoate

Procedure

30 gm (0.103M) ethyl-o-nitrophenylacetylacetoacetate was added over a period of 15-20 minutes to a saturated ammoniacal ethanol solution (prepared by bubbling NH3 gas into 400 cc. absolute alcohol for 15-20 minutes while cooling the solution to 0°-5° C.). The orangy mixture was stirred for 1 hour at 5°-10° C. and then left in the refrigerator overnight. The ethyl-γ-2-nitrophenylacetoacetate crystals formed were filtered and dried in vacuum. Additional solid was obtained after evaporation of the filtrate and washing with water to remove any amide formed.

Workup

  1. customprepared
  2. customby bubbling NH3 gas into 400 cc
  3. temperatureabsolute alcohol for 15-20 minutes while cooling the solution to 0°-5° C.)
  4. waitleft in the refrigerator overnight

Sources & evidence

ORD record
ord-96fdeb762da441bbb267f585204fcc57
Source dataset
uspto-grants-1978_01
Patent number
US04067872

Reaction notes

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