Hydrochloric Acid → 2-Chloroethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

HRID 1284913Notes

Reaction equation

HRID 1284913 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][Cl:21])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].Cl>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][Cl:21])=[O:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 1086052-Chloroethyl acetoacetate

Product 1

HCID 540552132-Chloroethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 Grams of 3-nitrobenzaldehyde and 11 g of 2-chloroethyl acetoacetate were dissolved in 100 ml of toluene, then under an ice-cooled condition, hydrogen chloride gas was introduced into the solution for 2 hours. The reaction mixture was allowed to stand at room temperature for 2 days, and was concentrated. The residue obtained was extracted with chloroform, then the chloroform layer was washed with a saturated sodium chloride aqueous solution and with a saturated sodium hydrogen carbonate aqueous solution and dried with anhydrous magnesium sulfate. Chloroform was removed by distillation and the residue was recrystallized from isopropanol to yield 10 g of 2-chloroethyl 2-(3-nitrobenzyliden)acetoacetate in the form of colorless needle-like crystals.

Workup

  1. additionwas introduced into the solution for 2 hours
  2. concentrationwas concentrated
  3. customThe residue obtained
  4. extractionwas extracted with chloroform
  5. washthe chloroform layer was washed with a saturated sodium chloride aqueous solution and with a saturated sodium hydrogen carbonate aqueous solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customChloroform was removed by distillation
  8. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-ae2f417460a2403c8bbc65fb5b23a000
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

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