Water → (4,4-Dimethyl-cyclohex-1-enyl)phenyl sulphone

HRID 648779Notes

Reaction equation

HRID 648779 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH2:3]1.S(OOS([O-])(=O)=O)(O)(=O)=[O:17].[K+].OOS([O-])=O.[K+].OS([O-])(=O)=O.[K+].[OH2:39]>CO>[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][C:5]([S:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:17])=[O:39])=[CH:4][CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 516920Potassium bisulfateHCID 23690007Potassium hydrogen persulfateHCID 23707502Potassium hydroxy sulfite2×HCID 57218155(4,4-Dimethylcyclohex-1-enyl)phenylsulphide

Product 1

HCID 70417592(4,4-Dimethyl-cyclohex-1-enyl)phenyl sulphone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of (4,4-dimethylcyclohex-1enyl)phenyl sulphide (1.66 g.) in methanol (30.5 ml.) cooled at 0° C., was treated dropwise with a solution of potassium hydrogen persulphate ("Oxone" brand, containing 2KHSO5. KHSO4.K2SO4 ; "Oxone" is a registered trademark) (9.0 g.) in distilled water (30.5 ml.) at such a rate as to maintain the reaction temperature below 5° C. After the addition was complete, the reaction was stirred for 64 hours. The methanol was then evaporated and the residue was diluted with water (50 ml.) before extraction with ether (3×100 ml.). The combined extracts were washed successively with saturated sodium bicarbonate solution (3×50 ml.) and water (3×50 ml.), dried (MgSO4) and evaporated. The residue obtained was purified by flash chromatography on silica, eluting with ether hexane (40:60 v/v), to give (4,4-dimethyl-cyclohex-1-enyl)phenyl sulphone (1.52 g.), m.p. 51°-53° C.; NMR (CDCl3): 0.9 (6H,s), 1.45 (2H,t), 2.0-2.3 (4H,m), 7.0 (1H,br s), 7.4-7.7 (3H,m) and 7.8-8.0 (2H,m).

Workup

  1. additioncontaining 2KHSO5
  2. temperatureto maintain the reaction temperature below 5° C
  3. additionAfter the addition
  4. customThe methanol was then evaporated
  5. additionthe residue was diluted with water (50 ml.) before extraction with ether (3×100 ml.)
  6. washThe combined extracts were washed successively with saturated sodium bicarbonate solution (3×50 ml.) and water (3×50 ml.)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue obtained
  10. customwas purified by flash chromatography on silica
  11. washeluting with ether hexane (40:60 v/v)

Sources & evidence

ORD record
ord-3e5dd3f8e19141f7a46e21b247784954
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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