Toluene → HCID 57123384, compound

HRID 2249089Notes

Reaction equation

HRID 2249089 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH:11](O)[CH2:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 14883924HCID 14883924, compound

Product 1

HCID 57123384HCID 57123384, compoundYield 95.1%

Procedure

1.50 Grams of 6-(4-bromophenylthio)-4-hydroxy-2-hexanone were dissolved in 100 mol of toluene, and 0.07 g of p-toluene sulfonic acid was added thereto. The resulting mixture was refluxed for 2.5 hours with stirring. After having been cooled, the mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution. Then the mixture was dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 1.41 g of 6-(4-bromophenylthio)-3-hexen-2-one. (trans : cis=2.8 : 1) (purity: 95.1%). The yield was 95.1%.

Workup

  1. temperatureThe resulting mixture was refluxed for 2.5 hours
  2. temperatureAfter having been cooled
  3. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThen the mixture was dried over anhydrous magnesium sulfate
  5. customRemoving the solvent from the mixture under reduced pressure

Sources & evidence

ORD record
ord-7a3e8aa47a7c4d12a0ff934222f09fed
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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