Cyclopentanepropanol → Cyclopentanepropanal

HRID 1071171Notes

Reaction equation

HRID 1071171 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Mn]([O-])(=O)(=O)=O.[K+]>ClCCl>[CH:1]1([CH2:6][CH2:7][CH:8]=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 69842CyclopentanepropanolHCID 516875Potassium PermanganateHCID 178418287HCID 178418287, compound

Product 1

HCID 11083898CyclopentanepropanalYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyclopentyl-1-propanol (15.0 g, 117 mmol) was dissolved in dichloromethane (600 mL) and treated with Celite (50 g) and pyridinium chlorochromate (50.0 g, 232 mmol). The reaction was stirred at room temperature for 24 hours. The reaction was found to be complete by thin layer chromatography (stain: potassium permanganate) and filtered through a pad of silica (dichloromethane) to afford 3-cyclopentyl-propionaldehyde as an oil (10.3 g, 70%). 1H NMR (CDCl3, 300 MHz) δ 11.1-10.8 (br s, 1H), 2.36 (t, 7.73 Hz, 2H), 1.8-1.5 (m, 9H), 1.09 (m, 2H).

Workup

  1. filtrationfiltered through a pad of silica (dichloromethane)

Sources & evidence

ORD record
ord-d685636d1b7b4d8594a1af34553cd5d2
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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