Cyclohexanecarboxaldehyde → 1-Cyclohexyl-7-chloro-1-hepten-3-one

HRID 67886

Reaction equation

HRID 67886 reaction equation
[Cl-:1].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:28]1([CH:34]=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1(C)C(C)=CC=CC=1>[CH:28]1([CH:34]=[CH:8][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][Cl:1])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 73680070[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

Product 1

HCID 572149341-Cyclohexyl-7-chloro-1-hepten-3-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2 parts of [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride and 1.2 parts of cyclohexanecarbaldehyde were combined in 45 parts of xylene. This suspension was maintained under a nitrogen atmosphere and was refluxed for about 4 hours until a clear solution formed. After cooling the solution to room temperature, xylene was removed at a temperature of about 60° C. and under reduced pressure, leaving a product mixture. This mixture was separated chromatographically on a silica column using as the elution solvent 50 percent by volume of Skelly B in benzene, to yield 1-cyclohexyl-7-chloro-1-hepten-3-one.

Workup

  1. temperatureThis suspension was maintained under a nitrogen atmosphere
  2. temperaturewas refluxed for about 4 hours until a clear solution
  3. customformed
  4. customxylene was removed at a temperature of about 60° C. and under reduced pressure
  5. customleaving a product mixture
  6. customThis mixture was separated chromatographically on a silica column

Sources & evidence

ORD record
ord-192fe84647684fc38c7548455c798d5e
Source dataset
uspto-grants-1982_08
Patent number
US04347192

Linked notes

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