3',5'-Dimethoxy-3,6-dihydro[1,1'-biphenyl]-2(1H)-one → 2-(3,5-Dimethoxyphenyl)cyclohexan-1-one

HRID 483004Notes

Reaction equation

HRID 483004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH:15]=[CH:14][CH2:13][C:12]2=[O:17])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H][H]>[Pd].C(O)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 133666713',5'-Dimethoxy-3,6-dihydro[1,1'-biphenyl]-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 133666722-(3,5-Dimethoxyphenyl)cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 23.6 g. 2-(3,5-dimethoxyphenyl)-4-cyclohexen-1-one, 300 ml. ethanol and 3 g. 10% Pd/C catalyst was hydrogenated at 40 psi (2.8 kg./cm.2). After hydrogen uptake ceased, the mixture was filtered, the filtrate evaporated in vacuo and the residue recrystallized from isopropyl ether to obtain 17 g. of product, M.P. 61°-62° C., lit. [J. Org. Chem., 27, 376 (1962)], M.P. 62.5°-63° C.

Workup

  1. additionA mixture of 23.6 g
  2. filtrationthe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. customthe residue recrystallized from isopropyl ether
  5. customto obtain 17 g

Sources & evidence

ORD record
ord-1d0424a4b9ad4c95b2aacc6f2cbcc98d
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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