HCID 59504314, compound → HCID 66652123, compound

HRID 418918Notes

Reaction equation

HRID 418918 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1>CO.N#N.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1

Participants

5

Reactant 1

HCID 59504314HCID 59504314, compound

Product 1

HCID 66652123HCID 66652123, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 947NitrogenSolvent

Procedure

Dissolve [2-(3-methoxy-phenyl)-4,4-dimethyl-cyclohex-1-enyl]-acetic acid methyl ester (4.3 g, 15 mmol) in methanol (135 ml), exchange with N2 3×, add palladium hydroxide 20% on activated carbon (0.84 g, 5.9 mmol). Add 60 psi of H2 at room temperature for 18 h. Filter off catalyst rinsing with methanol, concentrate filtrate to give the title compound (3.8 g, 88%): 1H NMR (CDCl3) δ 7.23-7.17 (m, 1H), 6.79-6.71 (m, 3H), 3.80 (s, 3H), 3.55-3.49 (t, 3H), 2.52-2.19 (m, 1H), 1.95-1.83 (m, 2H), 1.72-1.21 (m, 6H), 1.02 (s,3H), 0.99, (s, 3H), 0.93 (s, 1H).

Workup

  1. additionAdd 60 psi of H2 at room temperature for 18 h
  2. filtrationFilter off catalyst
  3. washrinsing with methanol
  4. concentrationconcentrate filtrate

Sources & evidence

ORD record
ord-a30c9fa283494f09879056a517b47a7f
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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