82617-90-1

Basic information

• Product Name: 2-chloroacetyl-3-phenyl-acrylic acid ethyl ester
• CAS NO: 82617-90-1
• Molecular Weight: 252.697
• Mol File: 82617-90-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-chloroacetyl-3-phenyl-acrylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloroacetyl-3-phenyl-acrylic acid ethyl ester(82617-90-1)
• EPA Substance Registry System: 2-chloroacetyl-3-phenyl-acrylic acid ethyl ester(82617-90-1)

Safety Data

• Hazardous Substances Data: 82617-90-1(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 100-52-7 benzaldehyde 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 36748-19-3 4,5-dihydro-5-phenyl-3(2H)-thiophenone 
• 38293-64-0 ethyl 2-phenyl-4-oxothiolane-3-carboxylate 

Relevant articles and documents

Knoevenagel condensation of aromatic aldehydes with ethyl 4-Chloro-3-oxobutanoate in ionic liquids

Knoevenagel condensations of aromatic aldehydes with ethyl 4-chloro-3-oxobutanoate catalyzed by morpholine/acetic acid were carried out in ionic liquids to give ethyl 2-chloroacetyl-3-arylpropenoates in 44-84percent yield after 0.5 to 2 h at room temperature (25-28 °C). These conditions represent a greener protocol for the Knoevenagel condensation than those using refluxing benzene or toluene as solvent. Aromatic aldehydes having aryl groups 4-chlorophenyl, 4-methoxyphenyl, 2-thiofuranyl, 2-furanyl, phenyl and 3,4-methylenedioxyphenyl gave (E)/(Z) diastereomeric ratios of products from 56/44 to 85/15. The two isomers of each compound were separately isolated and characterized. The structure of the (E)-isomer of ethyl 2-chloroacetyl-3-(3',4' methylenedioxyphenyl)propenoate was determined by X-ray crystallography and an unequivocal methodology of (E)/(Z)-structural analysis by 13C NMR (nuclear magnetic resonance) is presented.