3-Chloro-2-methyl-1-propene → (2-methyl-prop-2-ene-1-sulfonyl)-benzene

HRID 987915Notes

Reaction equation

HRID 987915 reaction equation
Cl[CH2:2][C:3]([CH3:5])=[CH2:4].[C:6]1([S:12]([O-:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Na+]>CO>[CH3:5][C:3](=[CH2:4])[CH2:2][S:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 112413-Chloro-2-methyl-1-propeneHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 684095(2-methyl-prop-2-ene-1-sulfonyl)-benzeneYield 98,128.297%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloro-2-methyl-propene (80 ml, 0.81 mmol) in dry methanol (450 ml) was stirred at room temperature during the addition of sodium benzenesulfinate (200 g, 1.22 mmol). The resulting suspension was refluxed for 20 hours, cooled to room temperature and concentrated in vacuo. The residue was poured onto water (600 ml) and the resulting solid filtered, washed three times with water (200 ml) and dried under vacuum for two days to give (2-methyl-prop-2-ene-1-sulfonyl)-benzene (156 g, 99%) which was used in the next step without further purification.

Workup

  1. temperatureThe resulting suspension was refluxed for 20 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was poured onto water (600 ml)
  4. filtrationthe resulting solid filtered
  5. washwashed three times with water (200 ml)
  6. customdried under vacuum for two days

Sources & evidence

ORD record
ord-d0b0ece8ca024c909e69289914d62213
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

Loading…