p-Toluenesulfonic acid → 8-Thiabicyclo(3.2.1)octan-3-one

HRID 387283Notes

Reaction equation

HRID 387283 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:8]1(C)C=CC(S(O)(=O)=O)=C[CH:9]=1>C1(C)C=CC=CC=1>[CH:6]12[S:1][CH:2]([CH2:8][CH2:9]1)[CH2:3][C:4](=[O:7])[CH2:5]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 2750548-Thiabicyclo(3.2.1)octan-3-oneYield 5,908.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tetrahydrothiopyran-4-one (19.1 g, 150 mmol), ethylene-1,2-diol (11.2 g. 180 mmol), toluene-p-sulfonic acid (0.5 g), and toluene (500 mL) was heated under reflux in a Dean-Stark apparatus for 1.5 h. The toluene was then removed by rotary evaporation, and the residue dissolved in ether and washed, first with 10% aqueous sodium hydroxide and then with water. The organic layer was dried (Na2SO4) and evaporated, and allowed to crystallize by standing in Et2O overnight, giving 24.4 g (93%) of the title compound.

Workup

  1. temperatureunder reflux in a Dean-Stark apparatus for 1.5 h
  2. customThe toluene was then removed by rotary evaporation
  3. dissolutionthe residue dissolved in ether
  4. washwashed, first with 10% aqueous sodium hydroxide
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated
  7. customto crystallize

Sources & evidence

ORD record
ord-42d12e8720074d6288bc654451ddaaff
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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