90581-52-5

Upstream product

• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 56535-98-9 2,5-diphenyl-[1,3]dioxolan-4-one 
• 17199-29-0 (S)-Mandelic acid 

Downstream Products

• 42052-51-7 (R)-3-hydroxy-1,3-diphenylpropane-1-one 
• 72237-28-6 (R)-(+)-3-acetoxy-3-phenylpropiophenone 
• 90507-50-9 (S)-((R)-2,2-Dimethyl-3-oxo-1-phenyl-propoxy)-phenyl-acetic acid 
• 90507-51-0 (S)-((S)-2,2-Dimethyl-3-oxo-1-phenyl-propoxy)-phenyl-acetic acid 
• 90507-48-5 (S)-((R)-3-Oxo-1,3-diphenyl-propoxy)-phenyl-acetic acid 
• 90507-49-6 (S)-((S)-3-Oxo-1,3-diphenyl-propoxy)-phenyl-acetic acid 
• 64471-43-8 (S)-α-cyclopentyl-α-hydroxy-α-phenylacetic acid 
• 64471-45-0 (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 20585-39-1 (2R)-2-Cyclohexyl-2-hydroxy-2-phenylacetic acid 

Relevant academic research and scientific papers

Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

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.

Stereoselective synthesis of α-alkyl-α-hydroxylphenylacetic acid. Part (I): Asymmetric alkylation of (S)-mandelic acid

An effective asymmetric synthesis of α-alkyl-α-hydroxyl phenyl acetic acid using benzaldehyde as steric hindrance agent has been accomplished by utilising the readily available and inexpensive chiral starting material, (S)-mandelic acid. The ee was determined by 1H NMR with Eu(hfc) 3 as shift reagent.

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).

Flash Vacuum Thermolysis of 1,3-Dioxolan-4-ones

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.