Water → ((2-Phenylallyl)sulfonyl)benzene

HRID 893183Notes

Reaction equation

HRID 893183 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)C=O>[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 moles as 1-chloro-2-phenyl-2-propene) is dissolved in dimethylformamide (100 cc). Sodium benzenesulphinate (8.2 g, 0.05 moles) is added and the mixture is heated to 70° C. for 2 h. The reaction mixture is poured into ice and water (350 g). It is stirred vigorously with pentane (150 cc) to extract the unreacted 1-chloro-2-phenyl-1-propene and 1-chloro-2-phenyl-2-propanol for 15 to 30 min until crystallization is complete. The crystals formed are filtered off, are washed with pentane (50 cc) and diisopropyl ether (50 cc), are drained thoroughly and are dried. 2-Phenyl-1-phenylsulphonyl-2-propene (9.8 g, 76%) is obtained. Mp=105° C.

Workup

  1. extractionto extract the unreacted 1-chloro-2-phenyl-1-propene and 1-chloro-2-phenyl-2-propanol for 15 to 30 min
  2. customuntil crystallization
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washare washed with pentane (50 cc) and diisopropyl ether (50 cc)
  6. customare dried

Sources & evidence

ORD record
ord-b3cb42430bc346d588f471b62d7be495
Source dataset
uspto-grants-1992_06
Patent number
US05123953

Reaction notes

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