Dimethyl Sulfoxide → HCID 178445620, compound

HRID 1707533Notes

Reaction equation

HRID 1707533 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11]Cl)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[C-:13]#[N:14].[Na+].CS(C)=O>O>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:13]#[N:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 178445619HCID 178445619, compound

Product 1

HCID 178445620HCID 178445620, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

38 g (0.20 mol) of trans-4-butylcyclohexylchloromethane, 12 g (0.24 mol) of NaCN and 40 cm3 of DMSO were heated up to 140° C. with a mantle heater while stirring. The reactant was cooled to room temperature, 1,000 cm3 of water was added, it was extracted with chloroform, and after washing with water the chloroform was extracted. The remaining oily substance was distilled under reduced pressure (b. p. 90°/3 mmHG) to obtain 34 g (0.19 mol) of trans-4-butylcyclohexylacetonitrile.

Workup

  1. extractionit was extracted with chloroform
  2. washafter washing with water the chloroform
  3. extractionwas extracted
  4. distillationThe remaining oily substance was distilled under reduced pressure (b. p. 90°/3 mmHG)

Sources & evidence

ORD record
ord-673dab62fca949f1b7517c9cc5071aaf
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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