Water → 1-Cyclohexyl-2-methyl-2-(4-methylbenzene-1-sulfonyl)propan-1-one

HRID 2226811Notes

Reaction equation

HRID 2226811 reaction equation
Cl[C:2]([CH3:12])([CH3:11])[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O-])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Na+].O>CS(C)=O>[CH:5]1([C:3]([C:2]([S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])([CH3:12])[CH3:11])=[O:4])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 3720192Sodium 4-methylbenzenesulfonateHCID 21466906HCID 21466906, compound

Product 1

HCID 218725811-Cyclohexyl-2-methyl-2-(4-methylbenzene-1-sulfonyl)propan-1-oneYield 27.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-chloro-1-cyclohexyl-2-methyl-1-propanone (30.0 g, 0.16 mole) and sodium p-toluenesulfonate (30.0 g, 0.17 mole) in dimethylsulfoxide was reacted with stirring at 60° C. for 20 hours. The reaction mixture was poured into cold H2O, and stirred at 0°-5° C. for 1 hour. The precipitate was filtered, washed with H2O and dried. The crude solid (18 g) was recrystallized from n-hexane/benzene to give 13.5 g of 2-cyclohexylcarbonyl-2-(p-toluenesulfonyl)propane as white needles.

Workup

  1. stirringstirred at 0°-5° C. for 1 hour
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O
  4. customdried
  5. customThe crude solid (18 g) was recrystallized from n-hexane/benzene

Sources & evidence

ORD record
ord-4b5ba1234e674761a1982c3db6499e77
Source dataset
uspto-grants-1994_09
Patent number
US05350660

Reaction notes

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