2-{Hydroxy-(3-methoxyphenyl)methyl}cyclooctanone → 2-(3-Methoxybenzyl)cyclooctanone

HRID 380114Notes

Reaction equation

HRID 380114 reaction equation
O[CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:11]>C(O)C.[Pd]>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:2][CH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:11]

Participants

4

Reactant 1

HCID 183672572-{Hydroxy-(3-methoxyphenyl)methyl}cyclooctanone

Product 1

HCID 183674112-(3-Methoxybenzyl)cyclooctanoneYield 42.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-{hydroxy-(3-methoxyphenyl)methyl}-cyclooctanone (6.0 g) and 10% Pd/C (2 g) in ethanol (120 ml) was stirred under H2 for 10 hours. The catalyst was filtered off and filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 2-(3-methoxybenzyl)cyclooctanone (2.4 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customfiltrate was evaporated in vacuo
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-359dd7f4185c4e369354f119f50008ca
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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