174867-39-1

Basic information

• Product Name: methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate
• Synonyms: methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate
• CAS NO: 174867-39-1
• Molecular Weight: 170.208
• Mol File: 174867-39-1.mol

Chemical Properties

• CAS DataBase Reference: methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate(174867-39-1)
• EPA Substance Registry System: methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate(174867-39-1)

Safety Data

• Hazardous Substances Data: 174867-39-1(Hazardous Substances Data)

Upstream product

• 148705-96-8 (+)-(αR)-α-hydroxycyclohex-1-eneacetonitrile 
• 4845-04-9 1-cyclohexene-1-methanol 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 18448-47-0 methyl cyclohex-1-ene-1-carboxylate 
• 79-11-8 chloroacetic acid 
• 174867-35-7 methyl (-)-(αR)-α-hydroxycyclohex-1-eneacetate 

Downstream Products

• 183322-97-6 (S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-cyclohex-1-enyl-ethanol 
• 183322-93-2 (S)-1-(cyclohexen-1-yl)-1,2-ethanediol 

Relevant articles and documents

Synthesis of (R)- and (S)-2-hydroxy-3-enoic acid esters

The synthesis of (R)- and (S)-2-hydroxy-3-enoic acid esters [(R)-1a-d and (S)-1a-c] is described. The (R) enantiomers were prepared by a Pinner synthesis from the corresponding (R)-cyanohydrins [(R)-2a-d], which in turn were obtained by R-oxynitrilase- (E.C. 4.1.2.10)-catalyzed addition of HCN to the α,β-unsaturated aldehydes 3a-d. For the preparation of the (5) enantiomers an inversion of the configuration had to be implemented. A critical evaluation of the two possible sequences: inversion of the configuration of the cyanohydrins followed by solvolysis of the nitrile function, and solvolysis of the cyanohydrins followed by inversion of the configuration of the resulting α-hydroxy esters, came out in favor of the latter pathway.