Water → ((2-Phenylallyl)sulfonyl)benzene

HRID 2372647Notes

Reaction equation

HRID 2372647 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH2:4].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].O.CCCCC>CN(C=O)C>[C:5]1([C:3](=[CH2:4])[CH2:2][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8003PentaneHCID 2723840Benzenesulfinic acid, sodium saltHCID 54639721-Chloro-2-phenyl-2-propene

Product 1

HCID 575471((2-Phenylallyl)sulfonyl)benzeneYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

This mixture (17 g, 0.05 molar as 1-chloro-2-phenyl-2-propene) is dissolved in DMF (100 cc). Sodium benzenesulphinate (8.2 g, 0.05 mole) is added and the mixture is heated to 70° C. for 2 h. The reaction mixture is poured into water and ice (350 g). It is stirred energetically with pentane (150 cc) to extract the 1-chloro-2-phenyl-1-propene and the 1-chloro-2-phenyl-2-propanol which have not reacted, for 15 to 30 min until crystallization is complete. The crystals formed are filtered off, are washed with pentane (50 cc) and with diisopropyl ether (50 cc) and are thoroughly drained and dried. 2-Phenyl-1-phenylsulphonyl-2-propene (9.8 g, 76%) is obtained. Mp=105° C.

Workup

  1. extractionto extract the 1-chloro-2-phenyl-1-propene
  2. customthe 1-chloro-2-phenyl-2-propanol which have not reacted, for 15 to 30 min until crystallization
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washare washed with pentane (50 cc) and with diisopropyl ether (50 cc)
  6. customdried

Sources & evidence

ORD record
ord-51a848415567423a843285872d355ade
Source dataset
uspto-grants-1992_03
Patent number
US05100460

Reaction notes

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