119555-96-3

Upstream product

• 67-56-1 methanol 
• 114703-29-6 1-(4-methoxyphenyl)-2,3,3-trichloro-1-hydroxy-2-propene 
• 38693-90-2 trans-3-(3-methoxyphenyl)acrylic acid methyl ester 
• 598-99-2 Methyl trichloroacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 96-34-4 methyl chloroacetate 
• 31459-98-0 methoxycarbonyl chloromethylene triphenyl phosphorane 

Downstream Products

• 1323412-91-4 (S)-2-chloro-3-(4-methoxyphenyl)propanoic acid 
• 1323413-03-1 C₁₁H₁₃ClO₃ 
• 1376213-47-6 (Z)-methyl 4-chloro-5-(4-methoxyphenyl)-3-oxopent-4-enoate 
• 1552-72-3 (Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid 
• 1376212-79-1 (Z)-methyl 4-chloro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate 

Relevant academic research and scientific papers

Titanium mediated olefination of aldehydes with α-haloacetates: An exceptionally stereoselective and general approach to (Z)-α-haloacrylates

An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol

Ru-catalyzed highly chemo- and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters under neutral conditions

Finely-tuned ruthenium-catalyzed highly chemoselective and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters at the carbonyl group was achieved under neutral reaction conditions (ee up to 97%). Both olefin and alkenyl halogen moieties, which are labile under hydrogenation conditions, remained untouched during the reaction.

Biocatalyzed enantioselective reduction of activated C=C bonds: Synthesis of enantiomerically enriched α-halo-β-arylpropionic acids

The enantioselective biocatalyzed reduction of the C=C bond of some (Z)-methyl α-halo-β-arylacrylates was investigated. The reaction was performed by baker's yeast fermentation and Old Yellow Enzymes 1-3 mediated biotransformations. The final products wer

Synthesis of dihalohydrins and tri- and tetra-substituted olefins

A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable α-halo-α,β-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as t

(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

(Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catal

Addition of α-halocarboxylic acid esters to para-substituted benzaldehydes in the presence of pentacarbonyliron

Pentacarbonyliron promotes addition of α-halocarboxylic acid esters at the carbonyl group of benzaldehyde and its para-substituted analogs. The substituent in the benzene ring strongly affects the process.

Synthesis of α-Halocinnamate Esters via Solvolytic Rearrangement of Trichloroallyl Alcohols

Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-α-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement.Micharl addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides.The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

Reactions of α,β-Unsaturated Carboxylates, Malonates and Phenylacetates with Manganese(III) Acetate in the Presence of Chloride Ions

The reaction of alkyl (E)-3-phenylpropenoates with manganese(III) acetate of Cl- ions gave alkyl (Z)-2-chloro-3-phenylpropenoates and alkyl 2,3-dichloro-3-phenylpropenoates.Ethyl (E)-2,3-diphenylpropenoate yielded ethyl 2,3-dichloro-2,3-diphenylpropanoate.Alkyl 3,3-diphenylpropenoates gave mainly alkyl 2-chloro-3,3-diphenylpropenoates.Ethyl 1-cyclohexenecarboxylate gave ethyl 1,2-dichlorocyclohexanecarboxylate.Dimethyl malonate yielded dimethyl dichloromalonate and tetramethyl 1,2-dichloro-1,1,2,2-ethanetetracarboxylate.Substituted malonates resulted in α-chloro derivatives.Methyl phenylacetates gave α-acetoxy derivatives.

Mechanism of Dehydroacetoxylation of Methyl 3-Acetoxy-3-aryl-2-halogenopropanoates

The rate of sodium methoxide-induced dehydroacetoxylation of the diesters p-RC6H4CH(OAc)CXHCO2Me (X= Br or Cl) has been studied as a function of the para-substituent.The results correspond to the para-substituent effects expected for proton abstraction from C-2, as estimated from the diastereoisomerisation of model compounds under similar conditions.This suggests that the elimination occurs via a carbanion mechanism, with C(2)-H bond-breaking rate-determining.The apparent insensitivity of the kinetic behaviour to configuration differences, together with the response of the reactions to the effect of the 3-substituent, is interpreted in terms of inductive stabilisation by the 2-halogen atom, which tends to localise the incipient negative charge at C-2, inhibiting distortion of its tetrahedral geometry.