268216-67-7

Upstream product

• 81036-97-7 (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one 
• 630-19-3 pivalaldehyde 
• 17199-29-0 (S)-Mandelic acid 
• 268216-65-5 cis-(2S,5R)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl-1-ol)-1,3-dioxolan-4-one 
• 268216-66-6 (2S,5R)-2-tert-Butyl-5-cyclohex-1-enyl-5-phenyl-[1,3]dioxolan-4-one 
• 1026552-59-9 (2S,5S)-2-tert-Butyl-5-cyclohex-2-enyl-5-phenyl-[1,3]dioxolan-4-one 

Downstream Products

• 20585-34-6 (S)-cyclohexylmandelic acid 

Relevant academic research and scientific papers

A large-scale asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid

A practical asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid has been demonstrated at pilot scale. The key step is the asymmetric aldol reaction using the Seebach approach of self-replication of stereochemistry. (S)-Mandelic acid was converted i

Stereoselective process for alkyl phenylglycolic acids

A process for preparing an alkyl phenylglycolic acid is disclosed. It follows the sequence of condensing a substituted acetaldehyde with mandelic acid to provide a 5-phenyl-1,3-dioxolan-4-one, which is condensed with an alkyl ketone or aldehyde to provide a 5-(1-hydroxyalkyl)-5-phenyl-1,3-dioxolan-4-one, which is dehydrated to a 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one. The 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one may be hydrolyzed and reduced to an α-alkylphenylglycolic acid or the hydrolysis and reduction steps may be reversed. The process enables the production of single enantiomers of cyclohexylphenylglycolic acid (CHPGA). An analogous process for racemic CHPGA is disclosed employing racemic mandelic acid and acetone. Novel intermediates in the process are also disclosed.