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

HRID 1375125Notes

Reaction equation

HRID 1375125 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-cyclohexene-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%, Melting point: 84 to 86° C.

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-760beff27e7a4616aff67cc92685c5bc
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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