3,5-Dimethylcyclohex-2-en-1-one → 3-Benzyl-3,5-dimethylcyclohexanone

HRID 1794191

Reaction equation

HRID 1794191 reaction equation
[CH2:1]([Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]=1>C(OCC)C.Cl[Cu]>[CH2:1]([C:11]1([CH3:10])[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 142913,5-Dimethylcyclohex-2-en-1-oneHCID 178419663HCID 178419663, compound

Product 1

HCID 222215123-Benzyl-3,5-dimethylcyclohexanoneYield 53%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a cooled (−20° C.) 1M benzylmagnesium bromide solution in diethyl ether (50 ml) under argon was added CuCl (0.52 g, 5.3 mmol) and the mixture was stirred for 5 min. Then a solution of 3,5-dimethyl-2-cyclohexen-1-one (12) (4.4 g, 35.1 mmol) in diethyl ether (15 ml) was added dropwise keeping the temperature below −10° C. The mixture was stirred for 2 h and quenched with 10% aqueous acetic acid (40 ml). The organic layer was separated, washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo afforded oily residue what was separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1). Cyclohexanone 13 (4.0 g, 53%) was obtained as a colorless oil.

Workup

  1. customthe temperature below −10° C
  2. stirringThe mixture was stirred for 2 h
  3. customquenched with 10% aqueous acetic acid (40 ml)
  4. customThe organic layer was separated
  5. washwashed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration in vacuo
  8. customafforded oily residue what
  9. customwas separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-600839a88a0b4a06ba14a9cfd5d75e29
Source dataset
uspto-grants-2006_04
Patent number
US07022729B2

Linked notes

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