10268-70-9

Upstream product

• 1429-05-6 phenyl 4-nitrobenzoate 
• 201230-82-2 carbon monoxide 
• 139-02-6 sodium phenoxide 
• 540-37-4 p-aminoiodobenzene 
• 150-13-0 4-amino-benzoic acid 
• 108-95-2 phenol 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 148964-72-1 4-[(4-octyloxybenzylidene)amino]benzoic acid phenyl ester 
• 1155917-95-5 macrocycle 1a 
• 1268444-35-4 C₂₁H₂₅NO₆ 
• 1268444-31-0 C₂₁H₂₅NO₃ 
• 1220918-50-2 4-{2-[2-(2-methoxyethoxy)ethoxy]acetylamino}benzoic acid phenyl ester 
• 488091-46-9 4-(4-octyloxybenzylamino)benzoic acid phenyl ester 
• 857887-62-8 4-[{(S)-2-[2-(2-Methoxy-ethoxy)-ethoxy]-propyl}-(2-nitro-benzenesulfonyl)-amino]-benzoic acid phenyl ester 
• 857887-63-9 4-{(S)-2-[2-(2-Methoxy-ethoxy)-ethoxy]-propylamino}-benzoic acid phenyl ester 
• 857887-60-6 4-(2-nitro-benzenesulfonylamino)-benzoic acid phenyl ester 
• 150-13-0 4-amino-benzoic acid 
• 108-95-2 phenol 
• 13791-83-8 4-[2-(4-Chloro-2-methyl-phenoxy)-propionylamino]-benzoic acid phenyl ester 

Relevant academic research and scientific papers

Regiospecific phenyl esterification to some organic acids catalyzed by combined Lewis acids

A new and efficient method for the preparation of various phenyl esters has been achieved by a simple reaction of an acid with phenol in the presence of anhyd. ZnCl2 and a catalytic amount of AlCl3. This combined Lewis acid also catalyzes the selective phenyl esterification to different dioic acids and is very simple and high yielding. Copyright Taylor & Francis Group, LLC.

Kinetic study of hydrolysis of benzoates. Part XXV. Ortho substituent effect in alkaline hydrolysis of phenyl esters of substituted benzoic acids in water

The second-order rate constants k2 for alkaline hydrolysis of phenyl esters of meta-, para-and ortho-substituted benzoic acids, X-C 6H4CO2C6H5 (X = H, 3-Cl, 3-NO2, 3-CH3, 4-NO2, 4-Cl, 4-F, 4-CH 3, 4-OCH3, 4-NH2, 2-NO2, 2-CN, 2-F, 2-Cl, 2-Br, 2-I, 2-CH3, 2-OCH3, 2-CF3, 2-NH2), and of substituted phenyl esters of benzoic acid, C 6H5CO2C6H4-X (X = 2-I, 2-CF3, 2-C(CH3)3, 4-Cl, 4-CH3, 4-OCH3, 4-NH2), have been measured spectrophotometrically in water at 25 °C. The substituent effect in alkaline hydrolysis of phenyl esters of para-substituted benzoic acids, similar to that for ethyl esters of para-substituted benzoic acids, was found to be precisely described by the Hammett relationship (p = 1.7 in water). The log k value for alkaline hydrolysis of phenyl and ethyl esters of meta-, para- and ortho-substituted benzoic acids, X-C6H4CO2R, was nicely correlated with log km,p,ortho = log ko + (ρ)m,pσ + (ρI)orthoσI + (ρ° R)orthoσ°R + δ orthoΕsB where σ, σI, σ°R are the Hammett polar, Taft inductive and Taft resonance (σ°R = σ° - σI) substituent constants, respectively. Ε SB is the steric scale for ortho substituents calculated on the basis of the log k values for the acid hydrolysis of ortho-substituted phenyl benzoates in water owing to the ortho substituent in the phenyl of phenyl benzoates. In water, the main factors responsible for changes in the ortho substituent effect in alkaline hydrolysis of phenyl and ethyl esters of ortho-substituted benzoic acids, X-C6H4CO2R, were found to be the inductive and steric factors while the role of the resonance term was negligible ((ρ°R)ortho ca. 0.3). In alkaline hydrolysis of substituted benzoates in neat water, the ortho inductive effect appeared to be 1.5 times and steric influence 2.7 times higher than the corresponding influences from the ortho position in the phenyl of phenyl benzoates. The contributions of the steric effects in alkaline hydrolysis of esters of ortho-substituted benzoic acids was found to be approximately the same as in acid hydrolysis of esters of ortho-substituted benzoic and acid esterification of ortho-substituted benzoic acids.

Chain-growth polycondensation for well-defined aramide. Synthesis of unprecedented block copolymer containing aramide with low polydispersity

Poly(p-benzamide) with a defined molecular weight and a low polydispersity and a block copolymer containing this well-defined aramide was synthesized. Phenyl 4-aminobenzoate, which would yield poly(p-benzamide), did not polymerize under the conditions of

Intramolecular general base catalyzed ester hydrolysis. The hydrolysis of 2-aminobenzoate esters

Rate constants have been obtained for the hydrolysis of the trifluoroethyl, phenyl, and p-nitrophenyl esters of 2-aminobenzoic acid at 50°C in H2O. The pseudo-first-order rate constants, kobsd, are pH independent from pH 8 to pH 4 (the pKa of the amine group conjugate acid). The 2-aminobenzoate esters hydrolyze with similar rate constants in the pH-independent reactions, and these water reactions are ～2-fold slower in D2O than in H2O. The most likely mechanism involves intramolecular general base catalysis by the neighboring amine group. The rate enhancements in the pH-independent reaction in comparison with the pH-independent hydrolysis of the corresponding para substituted esters or the benzoate esters are 50 - 100-fold. In comparison with the hydroxide ion catalyzed reaction, the enhancement in kobsd at pH 4 with the phenyl ester is 105-fold. Intramolecular general base catalyzed reactions are assessed in respect to their relative advantages and disadvantages in enzyme catalysis. A general base catalyzed reaction can be more rapid at low pH than a nucleophilic reaction that has a marked dependence on pH and the leaving group.

Substituent effects on the base-catalysed hydrolysis of phenyl esters of para-substituted benzoic acids

Seventeen model phenyl esters of 4-substituted benzoic acids were synthesised by the reaction of substituted benzoyl chlorides with phenol in aqueous alkaline solutions (Schotten-Baumann reaction), in pyridine (Einhorn reaction), or by the reaction of substituted benzoic acids with phosphorus oxychloride. Structures and purity of the model compounds were confirmed by 1H NMR and 13C NMR spectroscopy as well as by HPLC and elemental analysis. Phenyl 4-aminobenzoate was synthesised by reduction of phenyl 4-nitrobenzoate in methanol on palladium. Kinetics of base-catalysed hydrolysis of model phenyl esters occurring by the BAc2 mechanism were measured by UV spectrophotometry in 50% (v/v) aqueous dimethyl sulfoxide solutions at 25°C under pseudo-first-order conditions, (c[NaOH] = 0.001-1.0 mol l-1). The addition of OH- to phenyl benzoates was used to establish the kinetic J-E acidity scale. Linear relation between J-E and log kobs with the slope near unity was found for all the model compounds. The kinetic constants of hydrolysis of phenyl esters of 4-substituted benzoic acids precisely obey the Hammett relationship (σp) with ρ = 2.44. Quantitatively comparable results have been obtained by application of Alter-native Interpretation of Substituent Effects theory (AISE) using the σi set of substituent constants.