HCID 21196524, compound → HCID 18367302, compound

HRID 1067114Notes

Reaction equation

HRID 1067114 reaction equation
O[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]>CO.CCOC(C)=O.[Pd].[OH-].[OH-].[Pd+2]>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Participants

5

Reactant 1

HCID 21196524HCID 21196524, compound

Product 1

HCID 18367302HCID 18367302, compoundYield 76.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 2-[hydroxy-(2-methoxyphenyl)methyl]-cyclohexanone (3.71 g), 10% Pd/C (wet) (1.0 g), and 20% Pd(OH)2/C (180 mg) in MeOH-EtOAc (2:1, 150 ml) was stirred under hydrogen atmosphere at room temperature for 28 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane-EtOAc 7:1) to give 2-(2-methoxybenzyl)cyclohexanone (2.65 g) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 7:1)

Sources & evidence

ORD record
ord-4b64e939b055410a93f6428e070f4e9b
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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