p-Toluenesulfinic acid → HCID 13178696, compound

HRID 1702005Notes

Reaction equation

HRID 1702005 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH:4]=[CH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([S:23]([OH:25])=[O:24])=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH:4]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH2:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 10818p-Toluenesulfinic acidHCID 5148256HCID 5148256, compound

Product 1

HCID 13178696HCID 13178696, compoundYield 99.5%

Procedure

A mixture of 10 g of 2,4-dichlorobenzalpinacolone, 7.3 g of p-toluenesulfinic acid, 4.1 g of NaH2PO3 and 70 ml of 90% aqueous alcohol was heated under reflux for 8 hours. After cooling, 400 ml of ice water was added to the reaction mixture and extracted with 500 ml of ethyl acetate. The organic solvent layer was washed with 400 ml of 5% sodium bicarbonate aqueous solution and 400 ml of ice water and evaporated under reduced pressure to give 16 g of the captioned compound (yield 99%). nD27 1.5563.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling
  4. extractionextracted with 500 ml of ethyl acetate
  5. washThe organic solvent layer was washed with 400 ml of 5% sodium bicarbonate aqueous solution and 400 ml of ice water
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-35afc016fcad401185b854c7b8ad4e4a
Source dataset
uspto-grants-1983_04
Patent number
US04379921

Reaction notes

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