p-Toluenesulfinic acid → 1-(4-Chlorophenyl)-4,4-dimethyl-1-p-toluenesulfonylpentan-3-one

HRID 1702004Notes

Reaction equation

HRID 1702004 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[CH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([S:22]([OH:24])=[O:23])=[CH:18][CH:17]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:7][C:8](=[O:13])[C:9]([CH3:10])([CH3:11])[CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10818p-Toluenesulfinic acidHCID 3060495-(4-Chlorophenyl)-2,2-dimethylpent-4-en-3-one

Product 1

HCID 131786941-(4-Chlorophenyl)-4,4-dimethyl-1-p-toluenesulfonylpentan-3-oneYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3 g of 4-chlorobenzalpinacolone, 2 g of p-toluenesulfinic acid and 15 ml of ethanol was refluxed for 8 hours and then allowed to stand at a room temperature overnight. The collection of the precipitated crystals gave 4.8 g of the captioned compound (yield: 94%). m.p. 170°-171° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe collection of the precipitated crystals

Sources & evidence

ORD record
ord-f90d87fc36924255b80a56140978378a
Source dataset
uspto-grants-1983_04
Patent number
US04379921

Reaction notes

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