6335-82-6

Usage

InChI:InChI=1/C14H11NO4/c16-14(19-13-4-2-1-3-5-13)10-11-6-8-12(9-7-11)15(17)18/h1-9H,10H2

Upstream product

• 108-95-2 phenol 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 139-02-6 sodium phenoxide 

Downstream Products

• 16035-91-9 4-nitrophenylacetanilide 
• 3229-70-7 phenolate 
• 93130-84-8 (4-Amino-phenyl)-acetic acid phenyl ester; hydrochloride 
• 104-03-0 4-nitrobenzeneacetic acid 
• 108-95-2 phenol 
• 93130-67-7 (4-Guanidino-phenyl)-acetic acid phenyl ester; compound with methanesulfonic acid 

Relevant academic research and scientific papers

Alkaline Hydrolysis of Aryl Phenylacetates and Aryl 4-Nitrophenylacetates. Evidence consistent with an Elimination-Addition Mechanism

Hydrolysis of the substituted phenyl esters of phenylacetic acid is found to be first order each in the ester and hydroxide ion.Hydrolysis is catalysed by general bases and the catalytic coefficients for the substituted phenoxides obey the Broensted relation with β +0.49.The rate of hydrolysis of the esters of 4-nitrophenylacetic acid is independent of in the range employed.Both series of reactions exhibit low solvent isotope effect and high sensitivity to substituents in the leaving group .These datasuggest an E1cB mechanism for the hydrolysis.The keten intermediate envisaged for such a mechanism has been trapped as the anilide when the reactions are conducted in aniline buffers, without any effect on the rate of hydrolysis for variations in .An increase in the DMSO content in the solvent decreases the rate of hydrolysis of the esters of 4-nitrophenylacetic acid, which is explained by an (E1cB)anion mechanism for the hydrolysis.Transfer to aqueous DMSO results in rate accelerations for the esters of phenylacetic acid which can be accounted for by either an (E1cB)Bion pair or (E1cB)reversible mechanism for the hydrolysis.

Hydrolysis of Esters and Amides in Strongly Basic Solution. Evidence for the Intermediacy of Carbanions

Kinetic studies of the decomposition of the carbaninons derived from a number of esters and amides of p-nitrophenylacetic acid in strongly basic solution have been carried out.Kinetic solvents isotop effects and the large Hammett ρ value for substituents on the aromatic ring of substituted phenyl esters of p-nitrophenylacetic acid suggest decomposition occurs by an E1cB mechanism.Furthermore, it appears that the carbanion can decompose by either an ionic or a free-radical mechanism, depeneding on the nucleofugality of the leaving group.An intermediate predicted to be 4-nitrophenyl ketone ha been detected spestroscopically in a number of cases.