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

HRID 1375121Notes

Reaction equation

HRID 1375121 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][CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[CH:13]1.Cl>O>[CH3:11][CH:12]1[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 2723840Benzenesulfinic acid, sodium saltHCID 109204694-Methyl-2-cyclohexenone

Product 1

HCID 223949304-Methyl-3-(phenylsulfonyl)-cyclohexan-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzenesulfinic acid sodium salt (3.0 g) was added to a solution containing 1.52 g of 4-methyl-2-cyclohexene-1-one and 9 ml of water. 1N Hydrochloric acid (18 ml) was added dropwise to the resulting solution. After stirring at room temperature for 24 hours, the crystals so precipitated were filtered and washed with water, isopropanol and cold ethyl ether. After recrystallization from isopropanol, 4-methyl-3-(phenylsulfonyl)-cyclohexan-1-one (m.p.: 71–74) was obtained in the form of white crystals. Yield: 72%

Workup

  1. customthe crystals so precipitated
  2. filtrationwere filtered
  3. washwashed with water, isopropanol and cold ethyl ether
  4. customAfter recrystallization from isopropanol

Sources & evidence

ORD record
ord-ec3de838a3d64b668355fea4efc13a9a
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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