69637-13-4

Basic information

• Product Name: Benzenepropanoic acid, a-ethenyl-b-hydroxy-
• CAS NO: 69637-13-4
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• Mol File: 69637-13-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-ethenyl-b-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-ethenyl-b-hydroxy-(69637-13-4)
• EPA Substance Registry System: Benzenepropanoic acid, a-ethenyl-b-hydroxy-(69637-13-4)

Safety Data

• Hazardous Substances Data: 69637-13-4(Hazardous Substances Data)

Upstream product

• 3724-65-0 2-butenoic acid 
• 100-52-7 benzaldehyde 
• 13688-54-5 3-butenoictrimethylsilylester 
• 13991-36-1 4-bromocrotonic acid 
• 625-38-7 but-3-enoic acid 
• 13991-36-1 4-bromocrotonic acid 
• 106-95-6 allyl bromide 
• 109751-81-7 4-trimethylsilyl-2-butenoate trimethylsilyl ester 
• 87121-06-0 1,1-bis(trimethylsilyloxy)-buta-1,3-diene 

Downstream Products

• 56949-94-1 methyl threo-2-(1-hydroxy-1-phenylmethyl)-3-butenoate 
• 56949-94-1 methyl erythro-2-(1-hydroxy-1-phenylmethyl)-3-butenoate 
• 154073-05-9 methyl 2-phenyl-2,5-dihydro-3-furancarboxylate 

Relevant articles and documents

SILYLCETENES ACETALS ISSUS D'ACIDES α,β-ETHYLENIQUES: PREPARATIONS ET APPLICATIONS EN SYNTHESE

The preparation of bis(trimethylsilyl)butadienyl acetal(I) and bis(trimethylsilyl)methylbutadienyl acetal (II) is reported; compound I reacts with phenyl aldehyde and titanium chloride to give linear and branched isomers of hydroxyacids.

Synthesis of α-alkenyl-β-hydroxy adducts by α-addition of unprotected 4-bromocrotonic acid and amides with aldehydes and ketones by chromium(II)-mediated reactions

The regioselective and diastereoselective chromium(II)-mediated reactions of 4-bromocrotonic acid or amides with aldehydes and ketones can proceed without the need to protect protic sites to generate the respective α-alkenyl-β-hydroxy adducts, i.e. formally the addition of the α-anion of a carboxylic acid or amide to an oxo-compound is featured.

Exclusive α-coupling in the aldol reaction of unsaturated trimethylsilyl esters: An efficient and practical direct synthesis of unsaturated β-hydroxy acids

The lithium enolates of trimethylsilyl but-3-enoate and 3-methylbut-3-enoate reacted with aldehydes and saturated or aromatic ketones at -70°C to give exclusively the α-condensation products in excellent yields. The unsaturated β-hydroxy acids thus obtained were directly identified, and the usual conversion into their methyl esters with diazomethane was not necessary. Unsaturated ketones underwent Michael reaction through α-addition leading to the unsaturated 5-oxo acids.

Dienediolates from Unsaturated Carboxylic Acids. Reaction with para-Substituted Benzaldehydes. Electronic Effects on Regioselectivity

Regioselectivity α/γ ratios for addition of the lithium dienediolate of crotonic acid to para-substituted benzaldehydes are subject to small electronic effects when reactions are carried out at low temperature, but strong influence by substituents is observed on heating for 1 h at 60 deg C.A linear correlation is then found between regiochemical ratios and ?p parameters.Stereoselectivity RR/RS ratios (33:66 to 43:57) for α-adducts obtained in the cold do not depend on the substituents.