2-Methoxycyclohexanone → Guaiacol

HRID 2397161Notes

Reaction equation

HRID 2397161 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]>[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9]

Participants

3

Reactant 1

HCID 1109982-Methoxycyclohexanone

Product 1

HCID 460Guaiacol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 800 mg. of 5% palladium on charcoal (half of which has been used for a previous dehydrogenation) in 100 gm. of distilled 2-methoxycyclohexanone was stirred and refluxed under a pressure of 9 p.s.i. After 5 hours approximately 75% of the ketone was converted. The reaction was stopped and the crude product separated by filtration. Distillation afforded a high yield of o-methoxyphenol with virtually no residue in the still pot. The catalyst can be reused with no additional fresh catalyst added.

Workup

  1. additionA suspension of 800 mg
  2. temperaturerefluxed under a pressure of 9 p.s.i
  3. customthe crude product separated by filtration
  4. distillationDistillation

Sources & evidence

ORD record
ord-fb8b28868e4b4c6c95e15d58a4ba2dda
Source dataset
uspto-grants-1977_05
Patent number
USRE029200

Reaction notes

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