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Evidence for the formation of 2-hydroxyethyl esters by reaction of fatty acids with diazomethane in diethyl ether

✍ Scribed by G. Graff; L.A. Anderson; L.W. Jaques; R.T. Scannell

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 575 KB
Volume: 53
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(90)90130-j

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✦ Synopsis

Alkylation of long-chain saturated, unsaturated and unsaturated hydroxy fatty acids with ethereal diazomethane was investigated. Upon reaction with ethereal diazomethane, fatty acids dissolved in a minimal volume of diethyl ether/methanol (9:1) produced 98---99% methyl ester. Omission of methanol caused the formation of 10---40% side products. The side products from octadeca-9,12-dienoic and 13-hydroxy-octadeca-9,11-dienoic acid were isolated and conclusively identified as 2-hydroxyethyl esters by ~3C-NMR spectroscopy and mass spectrometry.

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