Water → 2-Methyl-2-phenyl-1,3-dithiolane

HRID 1415306Notes

Reaction equation

HRID 1415306 reaction equation
[CH:1]([SH:4])([SH:3])[CH3:2].C([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.[CH3:14][C:15]1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:2][C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][CH2:15][CH2:14][S:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7410AcetophenoneHCID 336451,1-Ethanedithiol

Product 1

HCID 219922-Methyl-2-phenyl-1,3-dithiolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethanedithiol (94 g) and acetophenone (120 g, 1 mole) were dissolved in benzene (500 ml), a trace of pTSA added and the solution refluxed under a Dean-Stark trap for 16 hours, until no more water collected. The solution was cooled, washed with ice-cold dilute caustic soda, then water, and reduced in volume to a viscous, colorless, or yellowish oil. This was distilled under vacuum to give 2-methyl-2-phenyl-1,3-dithiolane as a colorless oil with an unpleasant odor, yield 120 g (61%).

Workup

  1. customcollected
  2. temperatureThe solution was cooled
  3. washwashed with ice-cold dilute caustic soda
  4. distillationThis was distilled under vacuum

Sources & evidence

ORD record
ord-103090b631b44456974d54f12e4e0e27
Source dataset
uspto-grants-1977_01
Patent number
US04004018

Reaction notes

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