Diethyl Ether → Ethyl 6-oxohexanoate

HRID 1816776Notes

Reaction equation

HRID 1816776 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

5

Reactant 3

HCID 3283Diethyl EtherHCID 357781Ethyl 6-hydroxyhexanoateHCID 178418287HCID 178418287, compound

Product 1

HCID 11171124Ethyl 6-oxohexanoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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.

Workup

  1. customthe insoluble material removed by filtration
  2. customThe filtrate was purified by silica gel chromatography (diethyl ether)

Sources & evidence

ORD record
ord-2e124303135d48458d0b1bba485cebe5
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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