Water → (4,4-Dimethylcyclohex-1-enyl)phenylsulphide

HRID 648778Notes

Reaction equation

HRID 648778 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.O.[C:11]1(C)[CH:16]=[CH:15][C:14]([S:17](O)(=O)=O)=[CH:13][CH:12]=1.C1(S)C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5]([S:17][C:14]2[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 57218155(4,4-Dimethylcyclohex-1-enyl)phenylsulphide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 4,4-dimethylcyclohexanone (1 g.), p-toluene sulphonic acid monohydrate (23 mg.) and thiophenol (0.81 ml.) in toluene (24 ml.) was heated at reflux for 9 hours with azeotropic removal of water using a Dean and Stark apparatus. The mixture was cooled, diluted with toluene (25 ml.) and extracted with saturated sodium bicarbonate solution (2×10 ml.), washed with water (3×10 ml.) and dried (MgSO4). Evaporation of the solvent gave (4,4-dimethylcyclohex-1-enyl)phenylsulphide as an oil (1.66 g.); NMR (CDCl3,90 MHz): 0.94 (6H,s), 1.45 (2H,t), 1.98 (2H,m), 2.18 (2H,m), 6.02 (1H,m) and 7.3 (5H,m).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with saturated sodium bicarbonate solution (2×10 ml.)
  3. washwashed with water (3×10 ml.)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-71102adc199b4559be15ef5d5078120f
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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