56015-90-8

Upstream product

• 100-51-6 benzyl alcohol 
• 122-59-8 2-phenoxyacetic acid 
• 621-88-5 phenoxyacetamide 
• 140-11-4 Benzyl acetate 
• 2065-23-8 methyl 2-phenoxyacetate 
• 19513-78-1 1-(4-methoxy-phenyl)-2-phenoxy-ethanone 
• 112445-76-8 4-methoxyphenyl 2-phenoxyacetate 
• 3598-16-1 2-phenoxyacetic acid sodium salt 
• 100-44-7 benzyl chloride 

Downstream Products

• 67631-95-2 1,1-dimethyl-2-(2-phenoxyacetamido)ethylamine 

Relevant academic research and scientific papers

Highly effective C-C bond cleavage of lignin model compounds

A highly effective method is developed for the C-C bond cleavage of lignin model compounds. The inert Cα-Cβ or Cα-Cphenyl bond of oxidized lignin model compounds was successfully converted to an active ester bond through the classic organic name reaction, Baeyer-Villiger (BV) oxidation, and thus acetal esters and aryl esters were produced in high yields (up to 99%) at room temperature. Next, K2CO3 catalyzed the alcoholysis of the resulting ester products at 45 °C, affording various useful chemical platforms in excellent yields (up to 99%), such as phenols and multifunctional esters. This method uses commercially available reagents, is transition-metal free and simple, but highly effective, and involves mild reaction conditions.

A rapid microwave-assisted esterification utilizing the Mukaiyama supported reagent

Microwave heating was applied to a modified Mukaiyama reagent supported on a PS-DVB resin to develop a rapid and efficient protocol for the solution-phase synthesis of esters and lactones starting from alcohol and carboxylic acids. The products were obtained in high purity (NMR analysis) after a simple resin filtration.

Efficient transesterification/acylation reactions mediated by N-heterocyclic carbene catalysts

Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification involving numerous esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with enol acetates in short reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with primary alcohols in the presence of alkyl-substituted NHC to efficiently form the corresponding esters. While primary alcohols are selectively acylated over secondary alcohols with use of enol esters as acylating agents, methyl and ethyl esters can be employed as protective agents for secondary alcohols in the presence of the more active alkyl-substituted NHC catalysts. The NHC-catalyzed transesterification protocol was simplified by generating the imidazol-2-ylidene catalysts in situ.

N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

(graph presented) Imidazol-2-ylidenes, a family of N-heterocyclic carbones (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl-or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.

Improved ester interchange catalysts

(equation presented) Mixed alkoxide/aryloxide clusters are long-lived and milder than previously reported ester interchange catalysts. They completely transform difficult substrates in a single synthetic operation with lower catalyst and reagent ester loadings. In addition to superior activities, these mixed clusters are kinetically less basic toward enolizable esters.

Esterification of carboxylic acid salts

Mono- or polycarboxylic acid esters are prepared by reacting a salt of such carboxylic acid with an organic halocompound, e.g., a (cyclo)alkyl, (cyclo)alkenyl, aryl or aralkyl halide, in an aqueous reaction medium, in the presence of a catalytically effective amount of a phase transfer catalyst, for example an onium salt.

Mild conversion of primary carboxamides into carboxylic esters

Primary carboxamides are converted into the corresponding alkyl carboxylates by treatment with dimethylformamide dimethylacetal in the appropriate alcohol at 25-45°C. Yields are very good to excellent.

Selective Activation of Primary Carboxylic Acids by Electron-rich Triarylbismuthanes. Application to Amide and Ester Synthesis under Neutral Conditions

On being heated in benzene in the presence of tris(methoxyphenyl)bismuthanes 1b-1e, primary carboxylic acids are selectively activated to couple with amines and alcohols to produce the corresponding amides and esters in satisfactory yields, while secondary, tertiary and aromatic carboxylic acids remain unaffected. 2-Benzylmalonic acid is similarly converted into its corresponding diamides and diesters, but 2,2-dibenzylmalonic acid suffers extensive decarboxylation and, in the presence of aromatic olefins, it undergoes a novel -type cycloaddition reaction to form 4-substituted 2,2-dibenzyl-4-butanolides in low to fair yields.

Electron-rich Triarylbismuthines as Selective Condensation Reagent under Neutral Conditions. Condensation of Aliphatic Carboxylic Acids with Amines and Alcohols

On heating with amines or alcohols in the presence of tris(2-methoxyphenyl)- or tris(2,6-dimethoxyphenyl)bismuthine, carboxylic acids bearing α-hydrogen are readily converted into the corresponding amides or esters in good yields while those without α-hydrogen remain intact.

Electrochemical generation and reactions of acyloxytriphenylphosphonium ions

Constant-current electrolysis, in an undivided cell, of Ph3P in the presence of a carboxylic acid in CH2Cl2 containing 2,6-lutidinium perchlorate as the supporting electrolyte was shown to generate the corresponding acyloxyphosphonium ion, Ph3P+-OCOR, which was converted in situ to esters, amides, and β-lactams under mild conditions.