Acetonitrile → 155380-13-5

HRID 1636998Notes

Reaction equation

HRID 1636998 reaction equation
[C:1](#[N:3])C.[Cl:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9]>CCOCC>[Cl:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](=[O:9])[C:1]#[N:3]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 30163952-(Chloromethyl)benzoyl chloride

Product 1

HCID 9812919155380-13-5Yield 79.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 98% cuprous cyanide (2.01 g), acetonitrile (40 ml) and 2-chloromethylbenzoyl chloride (3.79 g) was heated under reflux with stirring for 4 hours. After the mixture was cooled by allowing it to stand, the mixture was diluted with ether, the precipitated insoluble materials were filtered off, and then the filtrate was washed successively with a saturated aqueous solution of sodium bicarbonate, water and saturated brine. The ether layer thus obtained was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain the crude product (3.49 g). The crude product was crystallized from ether-haxane to give the title compound (2.85 g, yield: 79.5%, white crystals).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter the mixture was cooled
  4. filtrationthe precipitated insoluble materials were filtered off
  5. washthe filtrate was washed successively with a saturated aqueous solution of sodium bicarbonate, water and saturated brine
  6. customThe ether layer thus obtained
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customto obtain the crude product (3.49 g)
  10. customThe crude product was crystallized from ether-haxane

Sources & evidence

ORD record
ord-c4bcb869291144198dd29eb151336cc3
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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