3-(5-Benzyloxypentyl)(1-hexenyl)benzene → 5-(3-Hexylphenyl)-pentanol

HRID 36152Notes

Reaction equation

HRID 36152 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:17]=[CH:18][CH:19]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:20]([C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:19]=[CH:18][CH:17]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 1

HCID 539255003-(5-Benzyloxypentyl)(1-hexenyl)benzene

Product 1

HCID 224078765-(3-Hexylphenyl)-pentanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 840 mgs of 3-(5-benzyloxypentyl)(1-hexenyl)benzene in 25 mls of methanol is hydrogenated over 5% palladium on carbon and then filtered through celite, concentrated, and chromatographed over silica gel (3:2 ether:hexane) to yield pure 5-(3-hexylphenyl)-pentanol.

Workup

  1. filtrationfiltered through celite,
  2. concentrationconcentrated
  3. customchromatographed over silica gel (3:2 ether:hexane)

Sources & evidence

ORD record
ord-9ce76c723e2049d39fbd341bd3dc9cc1
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Reaction notes

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