Ethyl-2-phenyl ethanoate

Some examples are shown in Figure 10.32 ethyl methanoate, propyl ethanoate, ethyl propanoate and phenyl ethanoate. 

Esters (4.48) have one carbon substituent at the carbonyl and one -OR group. They are formed from acids and alcohols (Figure 4.11), and the name of the ester is a combination of the acid and alcohol names. The name of the alcohol used the form of a substituent, methyl, ethyl, phenyl, etc., and the acid part now takes the suffix -oate, to indicate the ester functionality. Thus 4.49 is methyl propanoate. The most common error that students make in naming esters is that they don t recognize the functional group and try to name them as substituted ketones. If you are finding the nomenclature of these difficult, it s often helpful to separate the ester into the acid and alcohol from which it was made. 4.50 was made from ethanoic (acetic) acid and 1-penta-nol hence, the name is 1-pentyl ethanoate or 1-pentyl acetate. In text, esters may be written as... 

Compare and contrast the reaction with cone. HNOj/conc. H2SO4 of phenyl ethanoate and ethyl benzoate. 

Of this product, 4.5 g in 30 cc of dry isopropyl alcohol are refluxed for 16 hours with 2.5 g of (3-chloroethyl dimethyl amine. The solution is cooled and filtered clear from the solid by-product. The solvent is removed under reduced pressure on the steam bath and the residue is washed with anhydrous ether. It is dissolved in ethyl acetate from which it crystallizes. It is the hydrochloride of (3-(dimethylamino)ethyl ester of 2-phenyl-2-( 1-hy-droxycyclopentyl) ethanoic acid, melting at 134° to 136°C. 

Ethanoate Ethyl Difluoro-phenyl-ElOa, 415 (CO -> CF2) ElOb, 178 (CO -> CF,)... 

Ethanoate Ethyl Diazo-(3-trifluoro-methyl-phenyl)- E14b/2, 1147 (Hydrazon-Ox.)... 

Butanoatc Methyl 3-F uoro-2-hydroxy-3-phenyl- ElOb, 150 (Oxirane + HF/NRjH) Ethanoate Ethyl Fluoro-(4-methoxy-phenyl)- F.lOb, 107 (OH - I ) Propanoate Ethyl 2-Fluoro-3-hydroxy-3-phcnyl- ElOb,. 454 (R -CHO + F —CH, — COOR) E10b2, 52 (Educt)... 

Ethanoate Ethyl (4.5-Dimethoxy-2-fluoro-phenyl)- ElOa. 289 (HgX -> F)... 

Exercise 18-48 The Michael-addition product that results from ethyl 3-phenyl-propenoate and diethyl propanedioate, in principle, also can be formed by sodium ethoxide-catalyzed addition of ethyl ethanoate to ethyl (2-carbethoxy)-3-phenyl-propenoate. Work out the course of this reaction along the lines of Equations 18-25 and 18-26 and explain why it is less likely to be successful than the addition of diethyl propanedioate to ethyl 3-phenylpropenoate. It will be helpful to compare the various possible acid-base equilibria involved in the two possible routes to the same Michael-addition product. 

Scheme 9.145. A representation of proton removal from the methyl group of ethyl ethanoate (ethyl acetate, CH3CO2CH2CH3) generating a resonance-stabilized carbanion. Attack of the latter at the carbonyl of ethyl benzenecarboxylate (ethyl benzoate, C6H5CO2CH2CH3) and ethyl ethanoate (ethyl acetate, CH3CO2CH2CH3) to yield, respectively, ethyl 3-phenyl-3-oxopropanoate and 3-oxobntanoate (ethyl acetoacetate, CH3COCH2CO2CH2CH3). An example of the Claisen condensation.

C2 7H2 9NO5S, N-Tosyl-2,12-ethano-2-ethyl-8-methoxy-1,4-methylene-1,2,3,4,5,6,12,13-octahydrophenanthridin-3-one, 40B, 292 C27H33N, 1,2,3,4,5,6,7,8-Octahydro-l,4 5,8-diisopropano-4,5-dimeth-yl-9-phenyl-acridine, 45B, 315... 

In certain cases symbols are used for groups of atoms. Common ones are Me for methyl, Et for ethyl, Pr for propyl, Bu for butyl, and Ph for phenyl. These symbols are sometimes called organic elements. So, for example, ethanol is EtOH, phenol is PhOH, and ethanoic acid is MeCOOH. 

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