Water → Methyl 4-(4-chlorophenyl)-4-oxobutanoate

HRID 462877Notes

Reaction equation

HRID 462877 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([CH2:15][CH2:14][C:13]([O:17][CH3:18])=[O:16])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 77264-ChlorobenzaldehydeHCID 8929Sodium Cyanide

Product 1

HCID 230774Methyl 4-(4-chlorophenyl)-4-oxobutanoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
35 °C

Procedure

A solution of 4-chlorobenzaldehyde (23.4 g) in dry dimethylformamide (DMF: 100 ml) was added over 10 minutes to a stirred mixture of sodium cyanide (4.0 g) and dry DMF (200 ml). After 5 minutes a solution of methyl acrylate (10.75 g) in dry DMF (100 ml) was added to the reaction mixture over 20 minutes. The temperature of the reaction mixture was maintained at 35° C. throughout both additions and then for a further 3 hours before it was poured into water and extracted with diethyl ether. The extracts were washed successively with water (several times), dilute sulphuric acid, aqueous sodium bicarbonate, and water, before drying over magnesium sulphate and concentration under reduced pressure to give methyl 3-(4-chlorobenzoyl)propanoate (24.4 g, 86%) as a yellow solid.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed successively with water (several times), dilute sulphuric acid, aqueous sodium bicarbonate, and water
  3. dry with materialbefore drying over magnesium sulphate and concentration under reduced pressure

Sources & evidence

ORD record
ord-fc7ca7ca86a14bc385cb2e719b699b7f
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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