p-Toluenesulfonic acid monohydrate → 1,3-Oxathiolane-2-methanol, 2-benzoate

HRID 13680Notes

Reaction equation

HRID 13680 reaction equation
CO[CH:3]([O:14][CH3:15])[CH2:4][O:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.C1(C)C=C[C:20]([S:23](O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:6]([O:5][CH2:4][CH:3]1[S:23][CH2:20][CH2:15][O:14]1)(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 116081762-Benzoyloxy-1,1-dimethoxy-ethane

Product 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoateYield 5,173.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aliquots of 2-benzoyloxyacetaldehyde dimethyl acetal (50.0 g) prepared according to Example 1,2-mercaptoethanol (20.4 g), p-toluenesulfonic acid monohydrate (0.90 g) and toluene (250 mL) were placed in a three-neck flask, followed by heating. By-produced methanol was distilled off with the solvent. After distilling off about 150 mL, the reaction mixture was cooled to room temperature, was washed with a saturated aqueous sodium hydrogen carbonate solution and water and was dried over anhydrous sodium carbonate. After filtration and vacuum distillation at 144-147° C. and at 0.60 mmHg, the target compound (54.9 g) was obtained in a yield of 100%.

Workup

  1. customwere placed in a three-neck flask
  2. temperatureby heating
  3. distillationBy-produced methanol was distilled off with the solvent
  4. distillationAfter distilling off about 150 mL
  5. washwas washed with a saturated aqueous sodium hydrogen carbonate solution and water
  6. dry with materialwas dried over anhydrous sodium carbonate
  7. filtrationAfter filtration and vacuum distillation at 144-147° C.

Sources & evidence

ORD record
ord-e25737a69e25401f8b9682ecf2ac7c36
Source dataset
uspto-grants-2010_06
Patent number
US07728152B2

Reaction notes

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