(4-Nitrophenyl)methyl 4-chloro-3-oxobutanoate → HCID 178520786, compound

HRID 652823Notes

Reaction equation

HRID 652823 reaction equation
[Cl:1][CH2:2][C:3](=[O:18])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6].[N:19]([O-])=[O:20].[Na+]>C(O)(=O)C.O>[OH:20][N:19]=[C:4]([C:3]([CH2:2][Cl:1])=[O:18])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 2

HCID 20196963(4-Nitrophenyl)methyl 4-chloro-3-oxobutanoateHCID 23668193Sodium Nitrite

Product 1

HCID 178520786HCID 178520786, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

In 100 ml of acetic acid is dissolved 50 g (0.184 mol, uncorrected for purity) of the crude p-nitrobenzyl γ-chloroacetoacetate obtained in 1), and the solution is cooled to 5° C. or lower, and a solution of 12.7 g (0.184 mol) of sodium nitrite in 50 ml of water is added dropwise thereto at 5° C. or lower over a period of an hour. After completion of the addition, the mixture is stirred for 30 minutes and poured into 600 ml of ice water and extracted with 300-ml and 200-ml portions of ethyl acetate. The organic layers are combined and washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to dryness to give 54.0 g of p-nitrobenzyl α-hydroxyimino-γ-chloroacetoacetate as an oil.

Workup

  1. customobtained in 1), and the solution
  2. waitat 5° C. or lower over a period of an hour
  3. additionAfter completion of the addition
  4. extractionextracted with 300-ml and 200-ml portions of ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9ba81ae68fa24f05aed6a34b563f9905
Source dataset
uspto-grants-1987_06
Patent number
US04673739

Reaction notes

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