Water → (2,2-Dichloro-3,3-dimethylcyclopropyl)acetonitrile

HRID 1981334Notes

Reaction equation

HRID 1981334 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[C:14]([CH3:16])([CH3:15])[C:13]2([Cl:18])[Cl:17])(=O)=O)=CC=1.[C-:20]#[N:21].[K+].O>CN(C)C=O>[Cl:18][C:13]1([Cl:17])[C:14]([CH3:15])([CH3:16])[CH:12]1[CH2:11][C:20]#[N:21]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 13313521HCID 13313521, compound

Product 1

HCID 13313532(2,2-Dichloro-3,3-dimethylcyclopropyl)acetonitrileYield 106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6.48 g of 2,2-dichloro-3,3-dimethylcyclopropylmethyl p-toluenesulfonate and 2.0 g of potassium cyanide were suspended in 20 ml of dimethyl formamide, and the mixture was heated at 100° C. for 24 hours with stirring. After cooling, 50 ml of water was added to the reaction mixture. The mixture was extracted with hexane. The hexane layer was washed with water, and dried over sodium sulfate. After drying, the hexane was evaporated under reduced pressure to give 3.8 g of 2,2-dichloro-3,3-dimethylcyclopropylacetonitrile, the desired compound shown above. The boiling point of the product was 96° to 98° C. at 14 mmHg.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with hexane
  3. washThe hexane layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter drying
  6. customthe hexane was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be4af018903341bd8ac5651fc55f3388
Source dataset
uspto-grants-1985_04
Patent number
US04514418

Reaction notes

Loading…