3-(4-Methoxyphenyl)-1-propanol → 3-(4-Methoxyphenyl)propanal

HRID 968818Notes

Reaction equation

HRID 968818 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 794063-(4-Methoxyphenyl)-1-propanolHCID 178418287HCID 178418287, compound

Product 1

HCID 111266073-(4-Methoxyphenyl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A methylene chloride solution (300 mL) of 3-(4-methoxyphenyl)-1-propanol (Aldrich, 15.0 g, 0.090 mol) was cooled to 0° C. and stirred. Pyridinium chlorochromate (Aldrich, 23.4 g, 0.108 mol) was slowly added to the solution which was then warmed to room temperature, placed under a drying tube and stirred over a weekend (approx. 72 hrs.). The reaction mixture was filtered through a pad of Florisil (Aldrich) and the filtrate was concentrated to give the crude product as a dark oil. Purification by flash chromatography (6:1 hexanes:ethyl acetate) gave the desired 3-(4-methoxyphenyl)propionaldehyde as a pale yellow oil.

Workup

  1. customplaced under a drying tube
  2. stirringstirred over a weekend (approx. 72 hrs.)
  3. filtrationThe reaction mixture was filtered through a pad of Florisil (Aldrich)
  4. concentrationthe filtrate was concentrated
  5. customto give the crude product as a dark oil
  6. customPurification by flash chromatography (6:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-aa1747f038d34514a76af7f06daa303a
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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