Benzoic ethyl esters

Toluene.—According to Renard,1 this compound, by electrolytic oxidation in alcoholic-sulphuric acid, forms benzaldehyde and phenose, C6H6(OH)6( ). According to Puls,2 there are produced in the same electrolyte, using a diaphragm and a platinum anode, benzaldehyde, benzoic acid, benzoic ethyl ester, and, as chief product, p-sulphobenzoic acid. Under the same conditions, Merzbacher and Smith3 had obtained a poor yield of benzoic ethyl ester. 

Benzoic Esters.—Tafel and Friedrichs,2 by conducting the electrolysis in alcoholic-aqueous sulpnuric acid at lead or mercury cathodes, obtained methyl benzyl ether and the ethyl benzyl ether from benzoic methyl and benzoic ethyl esters respectively. Mettler,3 by a similar arrangement, obtained chiefly benzyl alcohol and some benzyl methyl ether from benzoic methyl ester. 

The same applies to esters where names of the type benzoic ethyl ester (in German Benzoesaureathylester ) are to be preferred to names of the type ethyl benzoate, when the acid has a long name. 

Propionic acid [79-09-4] M 74.1, b 141 , d 0.992, n 1.3865, n25 1.3843, pK 5-6.8 (Ho scale, aq H2SO4), pK2 4.88. Dried with Na2S04 or by fractional distn, then redistd after refluxing with a few crystals of KMn04. An alternative purification uses the conversion to the ethyl ester, fractional distn and hydrolysis. [Bradbury J Am Chem Soc 74 2709 1952.] Propionic acid can also be heated for 0.5h with an amount of benzoic anhydride equivalent to the amount of water present (in the presence of Cr03 as catalyst), followed by fractional distn. [Cham and Israel 7 C/iem 5oc 96 I960.]... 

Ethyl Acetoacetate. -The e. planation of the manner in which this substance is produced has been given in the account of the preparation. The result was anived at, not by the iscila-tion of the intermediate compound formed by the union of ethyl acetate with sodium ethylate, but by analogy with the behaviour of benzoic methyl ester with sodium benzylate, which gave the same additive product as that obtained by combining benzoic benzyl ester with sodium methylate, showing that such combinations could occur,... 

Benzoic acid, 4-amino-3-methyl-, ethyl ester]... 

A. Ethyl 4-Amino-3-(methylthiomethyl)benzoate [Benzoic acid, 4-amino-3-[(methylthio)methyl]-]. A 1-1., three-necked, round-bottomed flask is fitted with a mechanical stirrer, a condenser topped with a gas-inlet tube, and a two-neckcd adapter holding a low-temperature thermometer and a 100-ml., pressure-equalizing dropping funnel. The flask is charged with 10.50 g. (0.10 mole) of ethyl p-aminobenzoate [Benzocaine Benzoic acid, 4-amino-, ethyl ester] (Note 1), 300 ml. of acetonitrile, and 100 ml. of dichloromethane, is flushed with nitrogen, and is then immersed in a 40% aqueous methanol-dry ice bath maintained between... 

BENZOIC ACID, 4-(ACETYLOXY)-, ETHYL ESTER [1303145-3], 59 BENZOIC ACID, 4-(ACETYLOXY)-,... 

METHYL ESTER [24262-66-6], 59 Benzoic acid, 4-amino-, ethyl ester (94-09-7], 15,73... 

Benzoic acid, 2-acetyloxy-, methyl ester, 63 Benzoic acid, 4-(acetyloxy)-, 59 BENZOIC ACID, 4-(ACETYLOXY)-, ETHYL ESTER, 59 BENZOIC ACID, 4-(ACETYLOXY)-, MFTHYL ESTER, 59 Benzoic acid, 4-ammo-, ethyl ester, 15 Benzoic acid, 4-armno-3-methyI-, ethyl ester, 15... 

SYNTHESIS OF ORTHO SUBSTITUTED ARYLBORONIC ESTERS BY IN SITU TRAPPING OF UNSTABLE LITHIO INTERMEDIATES 2-(5,5-DIMETHYL-l,3,2-DIOXABORINAN-2-YL)BENZOIC ACID ETHYL ESTER... 

Benzoic acid, 2-(5,5)- dimethyl-1,3,2-dioxaborinan-2-yl)-, ethyl ester (346656-34-6)... 

CN 2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester... 

CN 4-[[6-[(aminoiminomethyl)amino]-l-oxohexyl]oxy]benzoic acid ethyl ester monomesylate... 

Kindler [Twi., 450( 1), 1926] has studied the alkaline hydrolysis of the ethyl esters of a number of substituted benzoic acids. The m-nitro compound was found to have a rate constant 63.5 times as fast as the unsubstituted compound. What relative rate constant is predicted for the reaction of p-methoxybenzoate by the Hammett equation The value based on experimental results is 0.214. 

Ethyl benzoate Benzoic acid, ethyl ester (8,9) (93-89-0)... 

The initial 6,ll-dihydrodibenz[b,e]oxepin-ll-one (7.1.9) is synthesized from the ethyl ester of 2-phenoxymethyl benzoic acid (7.1.7), which is easily synthesized by reacting ethyl 2-bromomethylbenzoate with phenol in the presence of a base. The resulting ester (7.1.5) is hydrolyzed into 2-phenoxymethylbenzoic acid (7.1.8), which is cyclized to 6,11-dihydrodibenz[b,e]oxepin-ll-one (7.1.9) by trifluoroacetic acid anhydride. 

---