Benzenebutanol → 4-Phenylbutanal

HRID 53559

Reaction equation

HRID 53559 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.[Cr](Cl)([O-])(=O)=O.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[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

6

Reactant 3

HCID 76889BenzenebutanolHCID 178418287HCID 178418287, compoundHCID 178418299HCID 178418299, compound

Product 1

HCID 290304-PhenylbutanalYield 22.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.2 mL (20.8 mmol) of 4-phenyl-1-butanol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at 0° C. was added 3.2 g of powdered 3 Å molecular sieves and then 5.37 g (24.9 mmol) of pyridinum chlorochromate (PCC). The resulting suspension was stirred at 0° C. for 1 h at which time an additional 2.16 g (10.0 mmol) of PCC was added and the reaction mixture was warmed to room temperature. After stirring at ambient temperature for 0.5 h, the reaction mixture was diluted with ether and filtered through celite to give 2.5 g of the crude product. Flash chromatography (elution with 5% ethyl acetate in hexane) yielded 700 mg of the aldehyde 119. 1H NMR was consistent with the structure.

Workup

  1. additionwas added
  2. filtrationfiltered through celite
  3. customto give 2.5 g of the crude product
  4. washFlash chromatography (elution with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4563dea700904bf38ba21d38dbfaeda7
Source dataset
uspto-grants-1997_04
Patent number
US05620971

Linked notes

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