144261-51-8

Basic information

• Product Name: Benzenepropanoic acid, b-hydroxy-a-methylene-, phenyl ester
• CAS NO: 144261-51-8
• Molecular Formula: C16H14O3
• Molecular Weight: 254.285
• Mol File: 144261-51-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, b-hydroxy-a-methylene-, phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, b-hydroxy-a-methylene-, phenyl ester(144261-51-8)
• EPA Substance Registry System: Benzenepropanoic acid, b-hydroxy-a-methylene-, phenyl ester(144261-51-8)

Safety Data

• Hazardous Substances Data: 144261-51-8(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 937-41-7 phenyl acrylate 
• 100-52-7 benzaldehyde 

Downstream Products

• 108-95-2 phenol 
• 937-41-7 phenyl acrylate 
• 1351533-81-7 (Z)-phenyl 2-(bromomethyl)-3-phenylacrylate 
• 1351533-88-4 (3S,4R)-phenyl 4-formyl-2-methylene-3-phenylhexanoate 

Relevant articles and documents

Enantio- and diastereoselective organocatalytic α-alkylation of aldehydes with 3-substituted 2-(bromomethyl)acrylates

The catalytic direct α-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to α-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

Different reaction patterns in the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone, phenyl acrylate and phenyl thioacrylate

In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.

The reactions of aryl acrylates under Baylis-Hillman conditions

The use of aryl acrylates in the Baylis-Hillman reaction is reported. In contrast to their alkyl counterparts these acrylates react very rapidly with aldehydes, often yielding cyclic products arising from reaction of the initial adduct with a second molecule of aldehyde.