Ketone synthesis by Gilman and van Ess
The ketone synthesis by Gilman and van Ess is a name reaction in organic chemistry , which was named after Henry Gilman (1893-1986) and Paul R. van Ess and published in 1933. The reaction is a method of converting a carboxylic acid into a ketone .
Overview reaction
The carboxylic acid is converted to a ketone by reaction with a lithium alkyl compound and subsequent hydrolysis :
mechanism
In the first step, the carboxylic acid reacts with a lithium alkyl compound , the carboxylic acid being deprotonated and the oxygen atom of the alcohol group attacking the lithium atom . Then another lithium alkyl compound is added, the lithium atom attaching to the oxygen atom of the carbonyl group . The alcoholate is protonated and hydrolyzed . In the last step, water is split off and a ketone is formed .
literature
- Alfred Hassner, C. Stumer: Organic Syntheses Based on Name Reactions (= Tetrahedron organic chemistry series . Volume 22 ). Elsevier, 2002, ISBN 978-0-08-043259-5 , pp. 130 ( limited preview in Google Book search).
Individual evidence
- ^ Henry Gilman, Paul R. van Ess: The Preparation of Ketones by the Carbonation of Organolithium Compounds In: Journal of the American Chemical Society . 55, No. 3, 1933, pp. 1258-1261, doi: 10.1021 / ja01330a070 .