Sodium toluene-4-sulphinate dihydrate → 1-Methyl-4-[(3-methyl-2-butenyl)sulfonyl]benzene

HRID 2049991Notes

Reaction equation

HRID 2049991 reaction equation
Br[CH:2]=[CH:3][CH:4]([CH3:6])[CH3:5].O.O.[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([S:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[Na+]>CN(C)C=O>[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([S:15]([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 23678556Sodium toluene-4-sulphinate dihydrateHCID 533952621-Bromo-3-methyl-1-butene

Product 1

HCID 8324051-Methyl-4-[(3-methyl-2-butenyl)sulfonyl]benzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (20 ml) was dissolved 1-bromo-3-methyl-butene(1.49 g, 10 m moles) and sodium p-toluenesulfinate dihydrate (2.5 g, 1.16 equiv.), the solution was stirred at room temperature for 3 hours. The product was isolated in the usual manner and recrystallized from n-hexane to give 1-(p-toluenesulfonyl)-3-methyl-2-butene (2.16 g, 96.4%), melting point: 71°-72° C.

Workup

  1. customThe product was isolated in the usual manner
  2. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-4a2892eeffa2423daffcb3a1d7eae73a
Source dataset
uspto-grants-1980_04
Patent number
US04199531

Reaction notes

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