Water → HCID 20360757, compound

HRID 2082840Notes

Reaction equation

HRID 2082840 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[C:5]([O:8][C:9]1[C:10]([Cl:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])(=[O:7])[CH3:6].[C-]#N.[Na+].O>CN(C)C=O>[C:5]([O:8][C:9]1[C:10]([Cl:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]([CH2:3][CH2:2][C:1]#[N:4])=[O:13])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 8929Sodium CyanideHCID 20360797HCID 20360797, compound

Product 1

HCID 20360757HCID 20360757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of redistilled acrylonitrile (20 g, 0.375 mole) in dimethylformamide (100 ml) was added dropwise to a stirred solution of 3-acetoxy-2-chlorobenzaldehyde (99.2 g, 0.5 mole) and sodium cyanide (12.25 g, 0.25 mole) in dimethylformamide (250 ml) at 35° C during 30 minutes. The mixture was stirred at 35° C for 4 hours, then poured into twice its own volume of water and the mixture was extracted with chloroform. The washed and dried extract was evaporated to give 3-(3-acetoxy-2-chlorobenzoyl)propionitrile.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe washed
  3. customdried
  4. extractionextract
  5. customwas evaporated

Sources & evidence

ORD record
ord-52bd29a530614fb0b68c81661fab6a62
Source dataset
uspto-grants-1978_04
Patent number
US04082843

Reaction notes

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