55538-79-9

Upstream product

• 127-09-3 sodium acetate 
• 50612-99-2 methyl 2-bromo-2-(4-methoxyphenyl)acetate 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 
• 108-24-7 acetic anhydride 
• 22979-36-8 methyl 2-diazo-2-(4-methoxypheny)acetate 
• 507-09-5 tiolacetic acid 
• 67-56-1 methanol 
• 123-11-5 4-methoxy-benzaldehyde 
• 6625-70-3 acetoxymalononitrile 
• 64-19-7 acetic acid 
• 20714-90-3 4-Methoxymandelic acid 
• 33646-40-1 4-methoxymandelonitrile 

Downstream Products

• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 
• 104383-29-1 methyl (S)-α-hydroxy-(4-methoxyphenyl)acetate 
• 32174-38-2 methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate 
• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 

Relevant academic research and scientific papers

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds

Hydrogen-bond-donor catalysts enable a variety of formal insertion reactions of diazo compounds. The role of the catalyst in the reaction system may vary depending on several factors, including the nucleophilicity of the diazo compound and the acidity of the insertion partner. Ureas and phosphoric acid derivatives can offer complementary reactivity patterns when selected as catalysts for selected O-H and S-H insertion reactions of aryl- and diazo-substituted esters.

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Urea-induced acid amplification: A new approach for metal-free insertion chemistry

The enhanced catalytic activity of difluoroboronate ureas proved to be essential as an acidity amplifier to promote metal-free O-H and S-H insertion reactions of α-aryldiazoacetates in high yield. This methodology was found to be generally applicable to a

One-portion synthesis of 2-acetoxy carbonyl compounds from aldehydes by using an acetylated masked acyl cyanide

α-Acetoxy esters or amides were synthesized directly and in one portion from aldehydes and alcohols or amines by one-carbon homologation using a masked acyl cyanide reagent bearing an acetyl group. Georg Thieme Verlag Stuttgart.

Study of the Rh2(OAc)4- or BF3·OEt2-mediated reaction of thioacetic S-acid with α-diazocarbonyl compounds

The Rh2(OAc)4-catalyzed reaction of methyl aryldiazo-acetates with thioacetic S-acid gives exclusively the S-H insertion products in high yields, while the corresponding reaction mediated by BF3·OEt2 gives O-est

Highly efficient chemo- and enantioselective enzymatic resolution of (+/-)-methyl O-acetylmandelates

Chemo- and enantioselective enzymatic hydrolysis of (+/-)-methyl O-acetylmandelates using AmanoPS has been described with very high yields and optical purity of the products.

Synthesis of Chiral α-Aryl-α-Hydroxyacetic Acids: Substituent Effects in Pig Liver Acetone Powder (PLAP) Induced Enantioselective Hydrolysis

Pig liver acetone powder (PLAP) catalyzed hydrolysis of alkyl α-acetoxy-α-arylacetates produces alkyl (S)-α-aryl-α-hydroxyacetates in 23-80percent enantiomeric purities.Enantioselectivity is dependent on the ester group of O-acetylmandelates.Substitution on the aromatic ring results in inferior selectivities.Only acetate group is hydrolyzed by PLAP while the ester functionality is found to be completely intact.

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.