Acid chlorides of aromatic acids

IV,187. REACTIONS AND CHARACTERISATION OF ACID CHLORIDES OF AROMATIC ACIDS... 

The physical properties of a few tjrpical acid chlorides of aromatic acids are collected in Table IV, 18 7). Some acid anhydrides are also included in this Table (compare Section 111,94). 

Acid chlorides of aromatic acids, 791 reactions of, 795, 1059 table of, 796 ... 

Tertiary aromatic alcohols are also prepared by the Grignard reaction from esters or acid chlorides of aromatic acids. 

Rice, F. A. H., Morganroth, W. Reaction of the acid chlorides of aromatic acids with bromine and silver oxide. J. Org. Chem. 1956, 21,... 

AROMATIC ACID CHLORIDES The chlorides of aromatic acids are prepared —... 

As an example of carbometallation, the 1,4-carbosilylation product 218 is obtained by the reaction of dienes, disilanes and acid chlorides of aromatic and a,/i-unsaturatcd acids at 80 °C. The phenylpalladium 216 is formed by the oxidative addition of benzoyl chloride, followed by facile decarbonylation at 80 °C, and reacts with butadiene to generate the benzyl-7i-allylic complex 217. Then, transmetallation with the disilane and reductive elimination afford 4-silyl-2-butenylbenzene 218 [92], Regioselective carbomagnesation of isoprene with allylic magnesium bromide 219 catalysed by Cp2TiCl2 gives 220, which is useful for terpene synthesis [93,94],... 

The C-acyl derivatives constitute the regular products. Thus, acylation of 5,5-dimethyl-3-(l-pyrrolidyl)-2-cyclohexen-l-one with acetyl chloride or with chlorides of aromatic acids affords 2-acyl derivatives.248" On the other hand, an analogous reaction with... 

Sulfonyl chlorides of aromatic carboxylic acids can be obtained from chlorides of the latter by treatment with sulfonating agents that do not produce water during the reaction.224... 

Imidoyl chlorides of aromatic carboxylic acids ( ). An equimolar mixture of the N-monosubstituted amide and phosphorus pentachloride is heated for 15-180 min at 60-140 C. After completion of the reaction, which is indicated by the cessation of hydrogen chloride evolution, the phosphoryl chloride is removed under reduced pressure, and the remaining imidoyl chloride is distilled under vacuum. The reported yield ranges from 41-96%, but generally yields of 80-90% are obtained. 

Aliphatic imidoyl chlorides react faster than the N-alkyl imidoyl chlorides of aromatic carboxylic acids, and arylimidoyl chlorides react the slowest. Electron-withdrawing groups attached to the aryl moieties retard the reaction while electron-donating groups attached to the aryl groups increase the rate of reaction. Likewise, a carbonyl group adjacent to the C=N bond decreases the rate of hydrolysis. Cyclic imidoyl chlorides react rather slowly with water, as evidence by the fact that 2-chloro-A -pyrroline can be recrystallized from aqueous acetone... 

Takeuchi Hasashi, Kakimoto Masa-Aki., Imai Yoshio. (2002). Novel Method for Synthesizing Aromatic Polyketones from Bis(arylsilanes) and Chlorides of Aromatic Bicarbonic Acids J. Polym. Sci. A, 40(16), 2729-2735. 

For example, the method for production of aromatic polyketones by means of Friedel-Craft polycondensation of bis (arylsilanes) with chlorides of aromatic dicarboxylic acids (isophthaloyl-,terephthaloyl-,4,4 -oxydibenzoylchloride) at 20 °C in environment of dissolvent (1,2-dichlor-ethane) in the presence of aluminum chloride is proposed in Ref [331], The polyketones have the intrinsic viscosity more than 0.37 deciliter/gram (at 30 °C, in concentrated H SO ), glass transition temperature is 120-231 °C and melting point lies within 246-367 °C. The polyketones start decomposing at a temperature of 400 °C, the temperature of 10% loss of mass is 480-530 °C. 

Should the chloride molecule contain certain groups which would cause the corresponding amide to have too high a melting point (nitro groups, halogens), an ester is prepared from the chloride by reaction with methanol or ethanol (see p. 252). Chlorides of aromatic acids yield solid acids on hydrolysis, which makes it possible simply to heat the tested substance with an aqueous solution of soda until dissolved and to precipitate the acid by acidification of the solution. 

Hammen equation A correlation between the structure and reactivity in the side chain derivatives of aromatic compounds. Its derivation follows from many comparisons between rate constants for various reactions and the equilibrium constants for other reactions, or other functions of molecules which can be measured (e g. the i.r. carbonyl group stretching frequency). For example the dissociation constants of a series of para substituted (O2N —, MeO —, Cl —, etc.) benzoic acids correlate with the rate constant k for the alkaline hydrolysis of para substituted benzyl chlorides. If log Kq is plotted against log k, the data fall on a straight line. Similar results are obtained for meta substituted derivatives but not for orthosubstituted derivatives. 

Compounds containing two primary amino groups attached to a benzene ring can be prepared by the reduction of dinitro compounds and of nitroanilines, usually with tin or stannous chloride and hydrochloric acid or with iron and very dilute hydrochloric acid. / ara-diamines may also be obtained by the reduction of aromatic amino-azo compounds (e.g., p-aminodimethylanihne from methyl orange, see Section IV,78). p-Phenylenediamine may also be prepared from p-nitroacetanilide reduction with iron and acid yields p-amino-acetaniUde,.which may be hydrolysed to the diamine. 

By passing a mixture of carbon monoxide and hydrogen chloride into the aromatic hydrocarbon in the presence of a mixture of cuprous chloride and aluminium chloride which acts as a catalyst (Gattermann - Koch reaction). The mixture of gases probably reacts as the equivalent of the unisolated acid chloride of formic acid (formyl chloride) ... 

From the acid chloride. The interaction of the acid chloride of au aromatic acid with the calculated quantity of an alcohol or a phenol aflFords a good yield of the ester, for example ... 

Acid Chlorides and Acid Anhydrides of Aromatic Adda, Table IV, 187. Aliphatic Esters, Table III, 106. 

Friedel-Crafts acylation of aromatic compounds (Section 12 7) Acyl chlorides and carboxylic acid anhydrides acylate aromatic rings in the presence of alumi num chloride The reaction is electrophil ic aromatic substitution in which acylium ions are generated and attack the ring... 

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