Diethyl Ether → Ethyl 6-oxohexanoate

Reaction equation

[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH3:13].CCOCC>ClCCl>[CH2:12]([O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[O:21])[CH3:13]

Participants

Procedure

To a solution of pyridinium chlorochromate (2.0 g) in dichloromethane (15 ml) was added a solution of 6-hydroxyhexanoic acid ethyl ester (1.0 g) in dichloromethane (1.5 ml) in one portion and stirred for 1.5 hours at ambient temperature. Ether (15 ml) was added to the reaction mixture, and the insoluble material removed by filtration and discarded. The filtrate was purified by silica gel chromatography (diethyl ether) to give 6-oxohexanoic acid ethyl ester (884.6 mg), as a pale green oil.