An efficient conversion of carboxylic acids to one-carbon degraded aldehydes via 2-hydroperoxy acids.
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.
Akakabe
Yoshihiko
Y
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi, Japan. akakabe@yamaguchi-u.ac.jp
Nyuugaku
Takeshi
T
D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013696:Temperature
D000447:Aldehydes; D002264:Carboxylic Acids; D006880:Hydroxy Acids; D002244:Carbon; D006851:Hydrochloric Acid; D010100:Oxygen