5-Phenyl-1-pentanol → Benzenepentanal

HRID 1781145Notes

Reaction equation

HRID 1781145 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 615235-Phenyl-1-pentanolHCID 178418287HCID 178418287, compound

Product 1

HCID 561886BenzenepentanalYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenylpentanol (15.0 g, 91 mmol) in methylene chloride was added pyridinium chlorochromate (24.6 g, 114 mmol) under an atmosphere of dry nitrogen at room temperature. After 18 hours, the mixture was filtered through a bed of Celite®, and purified by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane to give the aldehyde in 57% yield.

Workup

  1. filtrationthe mixture was filtered through a bed of Celite®
  2. custompurified by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-46ec9658e6fe46a7a019861f41f306d6
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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