2-Anisic acid

Manufacturing process Usually made by methylation of meto-cresol followed by oxidation of MCME using a strong oxidizing agent such as KMn04 

Another route is starting with m-nitrobenzoic acid, reduction and diazotization as in case of m-anisic aldehyde 

Again m-anisic acid demand is yet not established. Some quantities are consumed in Japan and China. Current consumption is estimated at 25-30 tpa. 

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An additional useful test is to distil the acid or its sodium salt with soda lime. Heat 0.5 g. of the acid or its sodium salt with 0 2 g. of soda lime in an ignition tube to make certain that there is no explosion. Then grind together 0-5 g. of the acid with 3 g. of soda hme, place the mixture in a Pyrex test-tube and cover it with an equal bulk of soda hme. Fit a wide dehvery tube dipping into an empty test-tube. Clamp the tube near the mouth. Heat the soda lime first and then the mixture gradually to a dull-red heat. Examine the product this may consist of aromatic hydrocarbons or derivatives, e.g., phenol from sahcyUc acid, anisole from anisic acid, toluene from toluic acid, etc. 

Ethyl Anisate.—Very similar to the methyl eSter of anisic acid is its ethyl ester. This is a crystalline compound of the formula... 

The ormethyl-salicylic acid melting at 99°, whUst the par -compound yields anisic acid melting at 184°. 

It readUy oxidises to anisic acid, melting at 184°, so that it should be kept in amber glass, well-stoppered bottles, in order to prevent oxidation. It forms a semi-carbazone melting at 203° to 204°, and two oximes, one melting at 63° and the other at 132°. 

Anisic ketone, CjqHj202, is found in oil of fennel. It is a liquid boiling at 263°, and having a specific gravity 1 095 at 0°. Its oxime melts at 72°. On oxidation it yields anisic acid. Its constitution is as follows —... 

Para-cresol methyl ether occurs naturally in oil of ylang-ylang and similar flower oils. It is also prepared synthetically, and forms a useful artificial perfume for compound flower odours. It is a liquid boiling at 175°, and, as stated above, yields anisic acid on oxidation. 

Anisic acid is p-methoxy-benzoic acid, C, H. COCHg. COOH.. It is found in aniseed oil, and also in Tahiti vanillas. It is a crystalline body-melting at 184°. 

Kinetics studies of acid-catalysed chlorination by hypochlorous acid in aqueous acetic acid have been carried out, and the mechanism of the reactions depends upon the strength of the acetic acid an<( the reactivity of the aromatic. Different groups of workers have also obtained different kinetic results. Stanley and Shorter207 studied the chlorination of anisic acid by hypochlorous acid in 70 % aqueous acetic acid at 20 °C, and found the reaction rate to be apparently independent of the hydrogen ion concentration because added perchloric acid and sodium perchlorate of similar molar concentration (below 0.05 M, however) both produced similar and small rate increases. The kinetics were complicated, initial rates being proportional to aromatic concentration up to 0.01 M, but less so thereafter, and described by... 

Kinetic studies at 25 °C showed that for benzene, toluene, o-, m-, and p-xylene, /-butylbenzene, mesitylene, 4-chloroanisole, and p-anisic acid in 51 and 75 % aqueous acetic acid addition of small amounts of perchloric acid had only a slight effect on the reaction rate which followed equation (100). At higher concentrations of perchloric acid (up to 0.4 M) the rate rose linearly with acid concentration, and more rapidly thereafter so that the kinetic form in high acid concentration was... 

Anisic acid, methyl ester [Benzoic acid, 4-methoxy-, methyl ester], 55, 40, 41 o-Amsidine [Benzenamine, 2-methoxy-], p-bromination of, 55, 23 [10] ANNULFNE, [ 1 l-Oxablcyclo[4 4 1]-undeca-l,3,5,7,9-pentaene], 55, 86 Anthramhc acid [Benzoic acid, 2-amino-], p-brominahon of, 55, 23 Apparatus, distillation of benzocyclopro-pene for, 55,13... 

A limited number of pure substances are available from NIST, primarily clini-cally-relevant compounds such as cholesterol, urea, uric acid, creatinine, glucose, cortisol, tripalmitin, and bilirubin (NIST SRM website). These compounds are certified for purity (greater than 99 %) and are used as primary calibrants in definitive methods for these clinical analytes (see below). Several additional pure substances are available for specific applications such as microchemistry, i.e. elemental composition (acetanilide, anisic acid, cystine nicotinic acid, o-bromobenzoic acid, p-fluoro-benzoic acid, m-chlorobenzoic acid), polarimetric standards (sucrose and dextrose), acidimetric standard (benzoic acid and boric acid). Only three pure substance NIST RMs are available for environmental contaminants, namely the chlorinated pesticides, lindane, 4,4 -DDT, and 4,4 -DDE. 

Parthenin (19) has at a concentration of 50 ppm no effect on the germination of the bean Phaseolus vulgaris but inhibits the development of radicles and hypocotyls (41). Similar effects were observed by Kanchan for Parthenlum hysteropherus and Eleusine coracana coleoptiles (42) and it was shown that besides parthenin (19), caffeic acid, vanillic acid, ferulic acid, chlorogenic acid an3 anisic acid were major constituents in P. hysteropherus (43). 

Benzoyl peroxide appears to decompose entirely by the radical mechanism, the reaction being rather insensitive either to solvent changes or to the addition of acid catalysts. The unsymmetrical peroxide, -methoxy-/> -nitrobenzoyl peroxide, behaves quite differently. It will decompose either by the polar mechanism or by the radical mechanism.821 The radical mechanism prevails in benzene and the acids produced are -nitrobenzoic and anisic in equal amounts. In the more polar solvents anisic acid is formed to a lesser extent than is >-nitrobenzoic acid, because the carboxy inversion reaction (rearrangement) competes successfully. The reaction is subject to acid catalysis... 

Anisamide, m54 Anisic acids, m57, m58, m59 Anidisines, m48, m49, m50 Anisole, m55 p-Anisoyl chloride, m60 p-Anisyl alcohol, m61 Anthranilamide, all2 Anthranilic acid, all8 Araboascorbic acid, i61 APDC, p282 Arsanilic acids, all3... 

Fig. 2.71. HPLC chromatogram of the neutral (a) and acidic fractions (b) and the acid-catalysed hydrolysed product of freshly squeezed cranberry juice (c) at 280 nnm. Peaks in a 1 = ( + )-cate-chin 2 = myicetin 3 = quercetin (added as internal standard). Peaks in b 1 = anthocyanin derivative I 2 = benzoic acid 3 = p-anisic acid 4 = quercetin (added as internal standard). Peaks in c 1 = ( + )-catechin 2 = anthocyanin derivative I 3 = anthocyanin derivative II 4 = benzoic acid 5 = anthocyanin derivative III 6 = p-anisic acid 7 = myricetin 8 = quercetin. Reprinted with permission from H. Chen et al. [188].

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