Diethyl Ether → 6-Methyl-6-hepten-2-one

HRID 1980608Notes

Reaction equation

HRID 1980608 reaction equation
[CH3:1][C:2](O)([CH2:5][C:6](C)=[CH2:7])[CH:3]=C.C([O:12][CH2:13][CH3:14])C>O1CCCC1>[CH3:3][C:2](=[CH2:1])[CH2:5][CH2:6][CH2:7][C:13](=[O:12])[CH3:14]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 124529713,5-Dimethylhexa-1,5-dien-3-ol

Product 1

HCID 1515096-Methyl-6-hepten-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,5-dimethylhexa-1,5-dien-3-ol (0.126 g; 10-3 mol) and dichloro-bis-(benzonitrile)-palladium(II) (0.0153 g; 0.04.10-3 mol) in tetrahydrofuran (7.5 cc) is kept at a temperature of the order of 20° C. under an inert atmosphere. After a reaction time of 5 hours, diethyl ether (50 cc) is added and the reaction mixture is then washed with water (7×10 cc). After drying of the organic layer over magnesium sulphate and evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa), 6-methylhept-6-en-2-one (0.125 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 reaction mixture is then washed with water (7×10 cc)
  3. dry with materialAfter drying of the organic layer over magnesium sulphate and evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-4e291d52386d4b65aa4bebbad1bf5be3
Source dataset
uspto-grants-1985_04
Patent number
US04510330

Reaction notes

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