Benzenebutanol → 4-Phenylbutanal

HRID 393358Notes

Reaction equation

HRID 393358 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 76889BenzenebutanolHCID 2724130Cornforth reagent

Product 1

HCID 290304-PhenylbutanalYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenylbutanol (1 g) in dichloromethane (35 mL) at 0° C. was added PDC (7.5 g). The resulting suspension was stirred for 2 h at room temperature. The reaction solution was then filtered through a pad of silica gel. Concentration of the filtrate and flash chromatography of the residue (20% ethyl acetate/hexanes) provided 4-phenylbutanal (237 mg) as a colorless oil.

Workup

  1. filtrationThe reaction solution was then filtered through a pad of silica gel

Sources & evidence

ORD record
ord-cb074581c4914473b793136777e8dfa7
Source dataset
uspto-grants-2004_10
Patent number
US06806369B2

Reaction notes

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