Ethyl-4-nitrobenzoate

These are pseudo-first-order rate constants for the alkaline hydrolysis of ethyl / -nitrobenzoate at 25°C. 

A solution of 19.5 g. (0.1 mole) of ethyl />-nitrobenzoate (Note 1) in 150 cc. of 95 per cent alcohol is placed in the reaction bottle of the catalytic reduction apparatus (p. 10) and 0.2 g. of platinum oxide catalyst (p. 92) is added. The mixture is shaken with hydrogen until three molecular equivalents have been absorbed. The time required is about seven minutes. The platinum is filtered off and the alcohol removed from the filtrate by distillation. The ethyl p-aminobenzoate, recrystallized from about 40 cc. of ether, melts at 89-90°. The yield is 15-16.5 g. (91-100 per cent of the theoretical amount). 

The results of the alkaline hydrolysis of ethyl nitrobenzoate at various times are in the table. Check first and second order mechanisms. 

The addition of carboxylic acids to olefins proceeds in solution in the presence of 10—4— 10 2 mol dm-3 of H3PW12O40 at 293-413 K with a selectivity of 100% (7). H2S04 is a less active catalyst than H3PW12O40 by a factor of 30-90. Esterification of /j-nitrobenzoic acid with ethanol has been carried out by using H2SO4 catalyst in an industrial process 160). In the presence of H3PW12O40, this reaction takes place with a yield >99% 160). At the end of the reaction, the reaction solution separates into two phases. The upper layer contains ethyl-/ -nitrobenzoate, toluene, and ethanol, and the lower layer consists of a solution of the heteropolyacid in ethanol. Consequently, the catalyst can be readily separated and reused. 

Ethyl -aminobenzoate has been prepared by the esterification of />-aminobenzoic acid1 and by the reduction of ethyl />-nitrobenzoate with ammonium sulfide.2 Although commercially the reagent used is usually iron and water in presence of a little acid, in the laboratory the catalytic reduction as described in the procedure is by far the most convenient. 

Nitrobenzoic acid, may be prepared by nitration of toluene and oxidation of the resulting /(-nitrotoluene, is esterified to the eorresponding ethyl ester by heating with absolute ethanol and a few drops of sulphurie acid. The resulting ethyl/>-nitrobenzoate is redueed with tin and hydrochloric acid to give the oflfieial compound. 

Synonyms Benzoic acid, p-nitro-, ethyl ester Ethyl-4-nitrobenzoate Ethyl nitrobenzoate, para ester p-Nitrobenzoic acid, ethyl ester... 

Ethyl nitrobenzoate, para ester. See Ethyl-p-nitrobenzoate N-Ethyl-3-nitro PABA CAS 2788-74-1... 

A number of mixed anhydrides react with alcohol in a rather peculiar manner. Thus benzoic nitrobenzoic anhydride and benzoic mesitylenccarboxylic anhydride yield benzoic acid together with ethyl nitrobenzoate and ethyl mcsitylcarboxylate, respectively, whereas benzoic cuminic anhydride forms both acids and both esters in conaderable quantity. ... 

Reaction of 1-N-pyrrolidinocyclohexene with -nitroacetophenone or ethyl -nitrobenzoate results in reduction of the nitro group to amino and formation of 2-N-pyrrolidinocyclohex-2-en-l-one67 Reduction of nitrobenzene to aniline is sluggish the enamine is converted to o-pyrrolidinophenol, not to a cyclohexenone. Literature procedures for preparation of enamines via titanium-amine complexes, Ti(NR2)4, often hampered by the somewhat tedious methods available for preparation of the titanium reagent. An improved enamine synthesis utilizes a stoichio-... 

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