Dimedone → Cyclohexanone, 3,3-dimethyl-

HRID 1189724Notes

Reaction equation

HRID 1189724 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=O)[CH2:6][C:4](=[O:5])[CH2:3]1.[H][H]>C(O)CO>[CH3:1][C:2]1([CH3:10])[CH2:9][CH2:7][CH2:6][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 31358DimedoneHCID 178418361HCID 178418361, compound

Product 1

HCID 76322Cyclohexanone, 3,3-dimethyl-Yield 4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Sasson et al. achieved reduction of dimedone via transfer hydrogenation in ethylene glycol as hydrogen donor in the presence of the homogenous catalyst RuCl2 (PPh3)3. Among a number of different reduction products 3,3-dimethylcyclohexan-1-one was obtained only in 4% yield which is an unacceptable low selectivity.

Sources & evidence

ORD record
ord-b3dd283b1c4e4d09aa9d53628da71494
Source dataset
uspto-grants-2014_03
Patent number
US08674143B2

Reaction notes

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