HCID 53700054, compound → 6-Phenyl-1-hexanol

HRID 743409Notes

Reaction equation

HRID 743409 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:15]1([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 53700054HCID 53700054, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 5201106-Phenyl-1-hexanolYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The whole of this 1-benzyloxy-6-phenyl-3,5-hexadiene was then treated with hydrogen in the presence of 250 mg of 5% w/w palladium-on-carbon in 40 ml ethanol at room temperature for 15 hours, the catalyst was removed by filtration and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.14 g (yield 88%) of 6-phenylhexanol as an oil.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ce7b817c5ea1432dbbf0a05b458ade46
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

Loading…