2-Mercaptoethanol → 1,3-Oxathiolane-2-methanol, 2-benzoate

HRID 640747Notes

Reaction equation

HRID 640747 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.[SH:16][CH2:17]CO>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:6]([O:5][CH2:4][CH:3]1[S:16][CH2:17][CH2:15][O:14]1)(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 15672-MercaptoethanolHCID 116081762-Benzoyloxy-1,1-dimethoxy-ethane

Product 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoateYield 102.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 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-51b8bd1cd4ba44f59afaf0f550273cd7
Source dataset
uspto-grants-2010_04
Patent number
US07692033B2

Reaction notes

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