4-Methylenecyclohexylmethanol → 4-Methylidenecyclohexane-1-carbaldehyde

HRID 1388122Notes

Reaction equation

HRID 1388122 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[CH2:10]=[C:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1>C(Cl)Cl>[CH2:10]=[C:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 138604-MethylenecyclohexylmethanolHCID 24503Dichromate ion

Product 1

HCID 158181364-Methylidenecyclohexane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To pydridinium dichromate (223 g., 0.59 mole) in 1 liter CH2Cl2, stirring under N2, was added dropwise 4-methylene-1-cyclohexanemethanol (50 g., 0.40 mole) in 75 ml. CH2Cl2 over a few minutes. After stirring for 21 hours at room temperature, the reaction mixture was heated at 60° C. for 24 hours. The reaction mixture was cooled, diluted with 400 ml. ether and decanted from solids. The solids were slurried with 400 ml. of fresh ether and decanted. The combined organic decants were filtered over fluorasil and diatomaceous earth and the filtrate concentrated in vacuo to an oil (41 g.) and distilled to yield title product, 13.6 g., b.p. 82°-90°/15-20 mm.

Workup

  1. stirringAfter stirring for 21 hours at room temperature
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with 400 ml
  4. customether and decanted from solids
  5. customof fresh ether and decanted
  6. customThe combined organic decants
  7. filtrationwere filtered over fluorasil and diatomaceous earth
  8. concentrationthe filtrate concentrated in vacuo to an oil (41 g.)
  9. distillationdistilled

Sources & evidence

ORD record
ord-99b3c224b8e648508accf0939f44d860
Source dataset
uspto-grants-1984_02
Patent number
US04430337

Reaction notes

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