56535-98-9Relevant articles and documents
Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones
Shcherbinin, Vitaly A.,Konshin, Valery V.
, p. 3570 - 3578 (2019/05/24)
An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.
Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity
Weng, Shiue-Shien,Li, Hsin-Chun,Yang, Teng-Mao
, p. 1976 - 1986 (2013/03/13)
A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.
Flash Vacuum Thermolysis of 1,3-Dioxolan-4-ones
Cameron, Tim B.,El-Kabbani, Fiesal M.,Pinnick, Harold W.
, p. 5414 - 5417 (2007/10/02)
Flash vacuum thermolysis of 1,3-dioxolane-4-ones yields aldehydes and ketones as the major products as the result of apparent decarboxylation of α lactones formed by collapse of a 1,3 dipole.When phenyl substituents are present, epoxides are also formed via the intermediacy of a carbonyl ylide.
