2-Cyclohexyl-2-acetoxyacetaldehyde dithiane → 2-Cyclohexyl-2-acetoxyacetaldehyde

HRID 1658573Notes

Reaction equation

HRID 1658573 reaction equation
S1CCCCS1.[CH:7]1([CH:13]([O:16][C:17](=[O:19])[CH3:18])[CH:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(#N)C.O.C(=O)([O-])[O-].[Cd+2]>[CH:7]1([CH:13]([O:16][C:17](=[O:19])[CH3:18])[CH:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 1

HCID 867335842-Cyclohexyl-2-acetoxyacetaldehyde dithiane

Product 1

HCID 109869602-Cyclohexyl-2-acetoxyacetaldehyde

Reagents, catalysts & solvents 3

HCID 10564Cadmium carbonate (CdCO3)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

The 2-cyclohexyl-2-acetoxyacetaldehyde dithiane (6.0 g.) in acetonitrile (300 ml.) was added to a stirred suspension of mercuric chloride (19.2 g.) and cadmium carbonate (11.6 g.) in acetonitrile (200 ml.) and water (4 ml.). The mixture was then stirred at 50° to 60°C. under nitrogen for 36 hours. The acetonitrile was removed in vacuo and the residue was washed several times with benzene and once with chloroform. Evaporation of the solvent and distillation of the residue gave 2-cyclohexyl-2-acetoxyacetaldehyde as a colourless oil, b.p. 120°C. (air bath)/0.5 mm., 3.9 g. (95%).

Workup

  1. customThe acetonitrile was removed in vacuo
  2. washthe residue was washed several times with benzene
  3. customEvaporation of the solvent and distillation of the residue

Sources & evidence

ORD record
ord-398c1d95cf934a18b950c0f015c87965
Source dataset
uspto-grants-1976_06
Patent number
US03965157

Reaction notes

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