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

HRID 1741380Notes

Reaction equation

HRID 1741380 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). MS (m/z): 247 (M+ +1) IR (Neat): 1700 cm-1NMR (CDCl3, δ): 1.0-2.4 (12H, m), 2.4-2.6 (1H, m), 2.8-3.0 (2H, m), 3.77 (3H, s), 6.6-6.8 (3H, m), 7.17 (1H, t, J=8 Hz)

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-ee528d0be8764d839603019d7faaa7c7
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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