p-Toluenesulfonic acid → 2-(4,4'-Difluorobenzhydrylidene)-1,3,5-trithiane

HRID 727863Notes

Reaction equation

HRID 727863 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)(O)[CH:9]2[S:14][CH2:13][S:12][CH2:11][S:10]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:8](=[C:9]2[S:10][CH2:11][S:12][CH2:13][S:14]2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 143292582-{Bis(4-fluorophenyl)hydroxymethyl}-1,3,5-trithiane

Product 1

HCID 143292842-(4,4'-Difluorobenzhydrylidene)-1,3,5-trithianeYield 89.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.0 g of 2-{bis(4-fluorophenyl)hydroxymethyl}-1,3,5-trithiane, 0.2 g of p-toluenesulfonic acid and 50 ml of benzene was refluxed with heating for 15 minutes by means of a Dean-Stark reflux condenser. After being cooled, the mixture was extracted with ethyl acetate and the extract was washed with a saturated aqueous sodium hydrogencarbonate solution. The washed extract was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure to obtain a material, which was recrystalized from cyclohexane to give 1.7 g of the desired compound.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 15 minutes by means of a Dean-Stark
  3. temperaturereflux condenser
  4. temperatureAfter being cooled
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe extract was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. extractionThe washed extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customto obtain a material, which
  11. customwas recrystalized from cyclohexane

Sources & evidence

ORD record
ord-b81efc2a34f544ef9b250ec22a72925d
Source dataset
uspto-grants-1991_09
Patent number
US05045562

Reaction notes

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