Benzene → Trans-4-(acetylthio)-2-phenyl-1,3-dioxane

HRID 381417Notes

Reaction equation

HRID 381417 reaction equation
[C:1]1([C@H:7]2[O:12][C@@H:11](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O-:27])(=[S:26])[CH3:25].[Na+].C1C=CC=CC=1>CN(C)C=O>[C:24]([S:26][C@@H:11]1[CH2:10][CH2:9][O:8][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:12]1)(=[O:27])[CH3:25]

Participants

5

Reactant 3

HCID 241BenzeneHCID 23700354HCID 23700354, compoundHCID 86583790cis-2-Phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane

Product 1

HCID 86583806Trans-4-(acetylthio)-2-phenyl-1,3-dioxaneYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
117.5 °C

Procedure

In 200 ml of dimethylformamide were dissolved 29.0 g (86.8 mmol) of cis-2-phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane and 17.0 g (149 mmol) of sodium thioacetate, and the solution was heated at 115 to 120° C. under a nitrogen atmosphere for 1 hour. After cooling, benzene was added to the reaction mixture and the mixture was washed with water, followed by evaporation of the solvent. The thus obtained brown residue was subjected to column chromatography using silica gel and the fractions eluted with a mixed solvent of benzene-hexane (2:1) were collected, followed by recrystallization from a mixed solvent of benzene-hexane to obtain 8.99 g (yield: 43%) of the title compound having a melting point of 95 to 96° C.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water
  3. customfollowed by evaporation of the solvent
  4. washthe fractions eluted with a mixed solvent of benzene-hexane (2:1)
  5. customwere collected
  6. customfollowed by recrystallization from a mixed solvent of benzene-hexane

Sources & evidence

ORD record
ord-a4f5c64bc10e4ceabe13d7d6b868c92e
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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