Toluene → Phenyl vinyl sulfone

HRID 1075496Notes

Reaction equation

HRID 1075496 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>O>[C:7]1([S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 81531Diisopropylethylamine

Product 1

HCID 79664Phenyl vinyl sulfoneYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

(β-chloroethylsulfonyl)benzene (4.09 g, 20 mmol) was added to 20 g of toluene, to this solution were added 3.00 g of 49% aqueous potassium carbonate solution (potassium carbonate 10.6 mmol) and 113 mg (1.0 mmol) or diisopropylethylamine, and the mixture was stirred for 4 hours at 40° C. Then, 10 g of water was added and the mixture was separated to an organic phase and aqueous phase. This aqueous phase was extracted by chloroform, and the resulted organic phase was combined with the previous organic phase, dried over magnesium sulfate, the solvents were distilled off, to obtain 2.76 g (yield 82.1%) of phenylvinylsulfone.

Workup

  1. customthe mixture was separated to an organic phase and aqueous phase
  2. extractionThis aqueous phase was extracted by chloroform
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvents were distilled off

Sources & evidence

ORD record
ord-1dbb0a1dfe0245d9aee1ffdbe9a5b91c
Source dataset
uspto-grants-1999_05
Patent number
US05902905

Reaction notes

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