Cyclopentanepropanol → Cyclopentanepropanal

HRID 1004643Notes

Reaction equation

HRID 1004643 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, 1 H), 2.36 (t, 7.73 Hz, 2 H), 1.8-1.5 (m, 9 H), 1.09 (m, 2 H).

Workup

  1. filtrationfiltered through a pad of silica (dichloromethane)

Sources & evidence

ORD record
ord-6ead7758382c4f53b1e7e5615b09b730
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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