p-Toluenesulfonic acid → 8-Thiabicyclo(3.2.1)octan-3-one
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureunder reflux in a Dean-Stark apparatus for 1.5 h
- customThe toluene was then removed by rotary evaporation
- dissolutionthe residue dissolved in ether
- washwashed, first with 10% aqueous sodium hydroxide
- dry with materialThe organic layer was dried (Na2SO4)
- customevaporated
- customto crystallize
Sources & evidence
- ORD record
- ord-42d12e8720074d6288bc654451ddaaff
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372875B2
Reaction notes
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