1,2-Ethanedithiol → 2-Benzoyloxymethyl-1,3-dithiolane

HRID 1081958Notes

Reaction equation

HRID 1081958 reaction equation
[C:1]([O:9][CH2:10][CH:11]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([SH:16])[CH2:14][SH:15]>C1(C)C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]1[S:16][CH2:13][CH2:14][S:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 109021,2-EthanedithiolHCID 108666642-oxoethyl Benzoate

Product 1

HCID 118173152-Benzoyloxymethyl-1,3-dithiolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-benzoyloxyacetaldehyde (example (5.65 g), 1,2-ethanedithiol (3 ml) and paratoluenesulfonic acid (200 mg) in toluene (250 ml) was heated at refluxing under water removal conditions using a Dean Stark apparatus for 4 hours. The mixture was cooled to room temperature, washed first with saturated aqueous NaHCO3 solution (1×60 ml), then with water (2×60 ml), and dried over reduced pressure. The residue was purified by chromatography on silica gel using hexane:ethyl acetate (9:1) as eluant to give 5.2 g of pure product which was characterized by 1H- and 13C-NMR spectroscopy.

Workup

  1. temperaturewas heated
  2. temperatureat refluxing under water
  3. customremoval conditions
  4. customfor 4 hours
  5. washwashed first with saturated aqueous NaHCO3 solution (1×60 ml)
  6. dry with materialwith water (2×60 ml), and dried over reduced pressure
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c555f2d61041444faea8d276d49b63f5
Source dataset
uspto-grants-1996_12
Patent number
US05587480

Reaction notes

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