2-Cyclohexen-1-one, 4,4-dimethyl- → Cyclohexanone, 4,4-dimethyl-

HRID 2075108Notes

Reaction equation

HRID 2075108 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Product 1

HCID 138166Cyclohexanone, 4,4-dimethyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4,4-Dimethylcyclohexanone was prepared by a procedure similar to that described in patent ref: PCT Int. Appl. 2005005456 20, January 2005. 4,4-Dimethylcyclohex-2-enone (3.5 g, 28.18 mmol) was dissolved in ethyl acetate (50 mL). The solution was shaken for 45 minutes under an atmosphere of hydrogen (10 p.s.i.). The completion of the reaction was established by GC-MS then the solution was filtered through a pad of celite and rinsed through with ethyl acetate. The solvent was removed under reduced pressure to give a clear colorless oil which crystallized on standing (3.45 gm, 97%). 1H NMR (400 MHz, CDCl3) δ 2.29 (m, 4H) 1.61 (m, 4H) 1.04 (s, 6H). MS calc 126.5, found 127.1 (M+H).

Workup

  1. filtrationthe solution was filtered through a pad of celite
  2. washrinsed through with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customto give a clear colorless oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-e30deb0585aa451ebfdc9ffd370b700b
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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