Carvone, (+-)- → 2-Methyl-5-(propan-2-yl)cyclohex-2-en-1-one

HRID 1014775

Reaction equation

HRID 1014775 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH:3]=1>C(Cl)Cl>[CH:9]([CH:5]1[CH2:6][C:7](=[O:8])[C:2]([CH3:1])=[CH:3][CH2:4]1)([CH3:11])[CH3:10]

Participants

3

Reactant 1

HCID 7439Carvone, (+-)-

Product 1

HCID 5212672-Methyl-5-(propan-2-yl)cyclohex-2-en-1-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of carvone (45 μL, 0.29 mmol) and rac-32 (8.0 mg, 0.0051 mmol, 1.8 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 48 h. Filtration of the reaction mixture and evaporation of the solvent gave 49 as a colorless oil (43 mg, 96%). 1H NMR36 (300 MHz, CDCl3): δ 6.72-6.69 (m, 1H), 2.53-2.47 (m, 1H), 2.37-2.27 (m, 1H), 2.13-1.99 (m, 2H), 1.85-1.78 (m, 1H), 1.73-1.72 (m, 3H), 1.54 (quin, 1H, J=6.6 Hz), 0.87 (dd, 6H, J=6.9 Hz, 0.9 Hz); 13C NMR (75.5 MHz, CDCl3): δ 200.6, 145.2, 135.2, 42.0, 41.9, 31.9, 29.8, 19.5, 19.4 15.6.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-c35edf05eae0450dbd0aa8081839ef44
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Linked notes

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