Water → HCID 178445620, compound

HRID 2254939Notes

Reaction equation

HRID 2254939 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+].O>CS(C)=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 962WaterHCID 8929Sodium CyanideHCID 178445619HCID 178445619, compound

Product 1

HCID 178445620HCID 178445620, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

In 40 cm3 of DMSO, 38 g (0.20 mol) of trans-4-butyl cyclohexylchloromethane and 12 g (0.24 mol) of NaCN were stirred and heated with a mantle heater to 140° C. The reaction product was cooled to room temperature, combined with 100 cm3 of water, extracted with chloroform, and washed with water. The chloroform was distilled off. The oily residue was subjected to vacuum distillation (b.p. 90° C./3 mmHg) to yield 34 g (0.19 mol) of trans-4-butylcyclohexyl acetonitrile.

Workup

  1. temperatureThe reaction product was cooled to room temperature
  2. extractionextracted with chloroform
  3. washwashed with water
  4. distillationThe chloroform was distilled off
  5. distillationThe oily residue was subjected to vacuum distillation (b.p. 90° C./3 mmHg)

Sources & evidence

ORD record
ord-c0e91e4953aa4f89b300817d77ba24e3
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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