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

HRID 1689573Notes

Reaction equation

HRID 1689573 reaction equation
[CH2:1]([O:3][CH:4](OCC)[CH2:5][O:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[SH:18]CCO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:7]([O:6][CH2:5][CH:4]1[S:18][CH2:2][CH2:1][O:3]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 118172582,2-diethoxyethyl Benzoate

Product 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 5-L, three-necked, round-bottomed flask fitted with a mechanical stirrer, a Dean-Stark apparatus, and a glass stopper is added 2-(benzoyloxy)acetaldehyde diethyl acetal (0.469 mol, 111.85 g, 1.0 equiv.), 2-mercaptoethanol (0.516 mol, 40.34 g, 1.1 equiv.), para-toluenesulfonic acid monohydrate (0.047 mol, 8.92 g, 0.1 equiv.) and toluene (3.5 L). The reaction was heated to reflux and stirred while monitoring progress by TLC. When determined to be complete, the reaction was allowed to cool to ambient temperature before washing with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated by rotary evaporation to give (+/−)-2-(benzoyloxymethyl)-1,3-oxathiolane as an oil (95.75 g, 90.9% yield). The crude product was advanced to the next reaction step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. washbefore washing with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-3ea92c4ddcb242dd905278dd209fdfed
Source dataset
uspto-grants-2012_04
Patent number
US08153416B2

Reaction notes

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