Diethyl Ether → 5-Methylcyclodec-5-en-1-one

HRID 1980610Notes

Reaction equation

HRID 1980610 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([CH:11]=[CH2:12])[OH:10])([CH3:3])=[CH2:2].C(OCC)C>O1CCCC1>[CH3:3][C:1]1[CH2:2][CH2:12][CH2:11][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 12677739HCID 12677739, compound

Product 1

HCID 538872325-Methylcyclodec-5-en-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-isopropenyl-1-vinylcyclohexan-1-ol (0.166 g; 10-3 mol) and dichloro-bis-(benzonitrile)-palladium(II) (0.038 g; 10-4 mol) in tetrahydrofuran (5 cc) is kept at a temperature of the order of 20° C. under an inert atmosphere. After a reaction time of 24 hours, diethyl ether (75 cc) is added and the mixture is then washed with water (5×15 cc). After drying over magnesium sulphate, filtration and evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa), 5-methylcyclodec-5-en-1-one (0.070 g) is obtained, which has the following characteristics:

Workup

  1. customis kept at a temperature of the order of 20° C. under an inert atmosphere
  2. washthe mixture is then washed with water (5×15 cc)
  3. dry with materialAfter drying over magnesium sulphate, filtration and evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-42877230e9314233880ed25bbc81ecd3
Source dataset
uspto-grants-1985_04
Patent number
US04510330

Reaction notes

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