Dimethyl Sulfoxide → 2-(3,4-Dichlorophenoxy)acetonitrile

HRID 67087

Reaction equation

HRID 67087 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18]#[N:19].CS(C)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][CH2:17][C:18]#[N:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 72583,4-DichlorophenolHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 29925912-(3,4-Dichlorophenoxy)acetonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 81.5 g of 3,4-dichlorophenol, 98.0 g of anhydrous K2CO3, 40.0 g of chloroacetonitrile and 100 ml of DMSO was stirred and heated to 70° C. after an initial period of ice cooling. The reaction mixture was heated at 70°-80° C. for 3 hours and the reaction mixture was then poured into 2500 ml of ice and water which resulted in crystal formation. The crystals were removed by filtration, washed with water and then dried overnight in a vacuum oven. The resulting solids were put in approximately 1 liter of boiling cyclohexane and treated with activated charcoal and then filtered. The filtrate was cooled to 10° C. and filtered, which gave 91.5 g of 3,4-dichlorophenoxyacetonitrile, m.p. 61°-62° C.

Workup

  1. temperatureThe reaction mixture was heated at 70°-80° C. for 3 hours
  2. customresulted in crystal formation
  3. customThe crystals were removed by filtration
  4. washwashed with water
  5. customdried overnight in a vacuum oven
  6. additiontreated with activated charcoal
  7. filtrationfiltered
  8. temperatureThe filtrate was cooled to 10° C.
  9. filtrationfiltered

Sources & evidence

ORD record
ord-e48ef224e84d46f3868e4a8d2f06dbcf
Source dataset
uspto-grants-1982_08
Patent number
US04344958

Linked notes

Loading…