Hydrochloric Acid → 4,4-Dimethyl-3-(phenylsulfonyl)-cyclohexan-1-one

HRID 1976748Notes

Reaction equation

HRID 1976748 reaction equation
[Na+].[C:2]1([S:8]([O-:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][C:12]1([CH3:19])[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[CH:13]1.Cl>O>[CH3:11][C:12]1([CH3:19])[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH:13]1[S:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-HCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 219991254,4-Dimethyl-3-(phenylsulfonyl)-cyclohexan-1-oneYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzenesulfinic acid sodium salt (5.98 g) was added to a solution containing 3 ml of 4,4-dimethyl-2-cyclohexen-1-one and 20 ml of water. Forty ml of 1N hydrochloric acid were added dropwise to the resulting mixture. The reaction mixture was stirred at room temperature for 24 hours. The crystals so precipitated were filtered and the solid, washed with water, isopropanol and cold ethyl ether. After recrystallization from isopropanol, 4,4-dimethyl-3-(phenylsulfonyl)-cyclohexan-1-one was obtained in the form of white crystals. Yield: 89%

Workup

  1. customThe crystals so precipitated
  2. filtrationwere filtered
  3. washthe solid, washed with water, isopropanol and cold ethyl ether
  4. customAfter recrystallization from isopropanol

Sources & evidence

ORD record
ord-7244d30f08874eb58faf18567731e4d9
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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