Document Detail

An efficient conversion of carboxylic acids to one-carbon degraded aldehydes via 2-hydroperoxy acids.
MedLine Citation:
PMID:  17485826     Owner:  NLM     Status:  MEDLINE    
After the formation of dianions of a carboxylic acid with lithium diisopropylamide, oxygen was bubbled into the solution to produce 2-hydroperoxy acid. Then the reaction mixture was acidified with a 2 N HCl solution and subsequently elevated to 50 degrees C to afford the aldehyde with the loss of one carbon atom. Even saturated (C(10)-C(20)) and unsaturated (C(18:1)) carboxylic acids were converted into the odd aldehydes (C(9)-C(19), C(17:1)) in high yields. This conversion was found to be an efficient method for the preparation of carboxylic acids (Cn) to one-carbon degraded aldehydes (Cn-1) via 2-hydroperoxy acids.
Yoshihiko Akakabe; Takeshi Nyuugaku
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Publication Detail:
Type:  Journal Article     Date:  2007-05-07
Journal Detail:
Title:  Bioscience, biotechnology, and biochemistry     Volume:  71     ISSN:  0916-8451     ISO Abbreviation:  Biosci. Biotechnol. Biochem.     Publication Date:  2007 May 
Date Detail:
Created Date:  2007-05-23     Completed Date:  2007-07-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9205717     Medline TA:  Biosci Biotechnol Biochem     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  1370-1     Citation Subset:  IM    
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi, Japan.
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MeSH Terms
Aldehydes / chemistry*
Carbon / chemistry*
Carboxylic Acids / chemistry*
Hydrochloric Acid / chemistry
Hydrogen-Ion Concentration
Hydroxy Acids / chemical synthesis*,  chemistry*
Oxygen / chemistry
Reg. No./Substance:
0/Aldehydes; 0/Carboxylic Acids; 0/Hydroxy Acids; 7440-44-0/Carbon; 7647-01-0/Hydrochloric Acid; 7782-44-7/Oxygen

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