HCID 59504489, compound → HCID 59504443, compound

HRID 418915Notes

Reaction equation

HRID 418915 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10](=[O:17])[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH:14]=2)[CH:6]=[CH:7][CH:8]=1>C(O)C.N#N.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][CH2:11][C:10]2=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 59504489HCID 59504489, compound

Product 1

HCID 59504443HCID 59504443, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 947NitrogenSolvent

Procedure

Dissolve 2-(3-methoxy-phenyl)-4,4-dimethyl-cyclohex-2-enone (13 g, 56.4 mmol) in ethanol (500 ml), exchange with N2 3×, and add 10% palladium on activated carbon (0.3 g, 2.82 mmol). Stir under atmospheric pressure of H2 over night. Filter off catalyst and concentrate to give the title compound (13.1 g, 99%): 1H NMR (CDCl3) δ 7.24-7.19 (m, 1H), 6.85-6.64 (m, 3H), 3.78 (s, 3H), 1.97-1.89 (m, 1H), 1.82-1.75 (m, 3H), 1.64-1.55 (m, 1H), 1.25-1.14 (m, 2H), 1.0 (s, 3H), 0.96 (s,3H).

Workup

  1. filtrationFilter off catalyst
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-3e76a85c014243bebc7b272dfcb82be5
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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