2-chlorobenzoic acid, from

In the first of the six papers [95] Hong and his students examined the photochemistry of 2-chlorobiphenyl in Ti02/H20 slurries, in the presence and absence of 02. They identified 12 aromatic products, 2-hydroxybiphenyl, the seven 2-chlorobiphenylols, 2-chlorobenzaldehyde, 2-chloroacetophe-none, benzoic acid, and 2-chlorobenzoic acid, from the photochemistry (Scheme 14). The hydroxyl radical clearly played a dominant role in the degradation. The disappearance of 2-chlorobiphenyl and its degradation... 

Willstatter s method (Volume I, pp. 278 285-286) to a-methyltropidine, i.e. (+ )-5-dimethylamino-l,3-cycloheptadiene (LXXXIV). Resolution of the latter with dibenzoyltartaric acid followed by (a) isomerization of each antimer into )3-methyltropidines (LXXXV), (b) hydrolysis, (c) partial hydrogenation of the cycloheptenone, and (d) Grignard reaction with the cycloheptanones (LXXXVI) gave the phenyl-, and p-chlorophenyl-l-cycloheptenes (LXXXVII). The product of oxidation, arising from (+ )-LXXXI V, contained the whole radioactivity, while the benzoic and p-chlorobenzoic acids from the levorotatory form were radioinactive. This proved that the whole label from ornithine-a-i C was either in C-1 or in C-5 in hyoscyamine (80, 81). 

Suggest a synthesis of the following compounds from the indicated starting material (a) 1,3,5-trichlorobenzene from aniline (b) 4-chlorobenzoic acid from aniline (c) 1-chloro-4-nitrobenzene from aniline (d) l-bromo-3-fluorobenzene from benzene (e) 3-chloroac-etanilide from benzene. 

It is also important to determine the point in a reaction sequence at which a substituent should be chemically modified. In the synthesis of para-chlorobenzoic acid from toluene, the methyl group is oxidized after it directs the chloro substituent to the para position. (orf/zo-Chlorobenzoic acid is also formed in this reaction.)... 

The use of hydrotropes, substances which possess the property of selectively enhancing the aqueous solubility of sparingly-soluble compounds, can afford an opportunity for mixture separation. Colonia, Dixit and Tavare (1998) describe an example of the use of a hydrotrope for the separation of the 0- and j -isomers of chlorobenzoic acid from a 42/58% mixture, a typical ratio for the product from an industrial reactor. Sodium butyl monoglycol sulphate, used as a 50% aqueous solution, is a suitable hydrotrope in which the ortho-... 

FIG. 4 Plots of vapor pressure of the crystalline substances versus the time required to become amorphous in mixtures with activated carbon. (O) At 25°C and atmospheric pressure ( ), at 40°C and reduced pressure. 1, Benzoic acid 2, o-hydroxybenzoic acid 3, w-hydroxybenzoic acid 4. p-hydroxybenzoic acid 5, o-chlorobenzoic acid 6, m-chlorobenzoic acid 7, p-chlorobenzoic acid. (From Ref. 13.)... 

Figure 6.2 The influence of polysorbate 20 concentration and pH on the solubility ratio, K, of 4-chlorobenzoic acid. From Collett and Koo [29].

Thus o-hydroxyphenyl-llthium cannot be obtained from o-bromophenol and lithium but, under proper conditions, o-bromophenol reacts with n-butyl-lithium to give a good yield of the lithium salt of o-hydroxyphenyl-hthium. An interesting application is to the preparation from m-bromochlorobenzene and M-butyl-lithlum of w-chlorobenzoic acid—an expensive chemical ... 

C bol the solution of re-butyl-hthium to — 35° in a Dry Ice - acetone bath and add, whilst stirring vigorously, a solution of 48 g. of ni-chlorobromo-benzene (Section IV,62) in 75 ml. of anhydrous ether. Stir for 8-10 minutes and pour the mixture with stirring on to a large excess of sohd carbon dioxide in the form of a Dry Ice - ether slush contained in a -htre beaker. Isolate the acid as detailed above for p-Toluic acid and recrystal-lise it from hot water. The yield of ni-chlorobenzoic acid, m.p. 150-151°, is 27 g. 

Amino-4-chlorobenzoic acid [2840 28-0] M 171.6, m 216-217 , pKesid)-2.7, pKeski)-2.9. Crystd from water. 

Chlorobenzoic acid [535-80-8] M 156.6, m 154-156°, 158°, dj 1.496, pK 3.82 (5.25 in 50% dimethylacetamide). Crystd successively from glacial acetic acid, aqueous EtOH and pet ether (b 60-80°). It also recrysts from CgH6 or Et20-hexane, and sublimes at 55° in a vacuum. [Anal Chem 26 726 1954] The methyl ester has m 21°, b 231°/atm. The S-benzyl thiouronium salt has m 164-165° (from EtOH) [Acta Chem Scand 9 1425 1955 J Chem Soc 1318 I960],... 

Chlorobenzoic acid [74-11-3] M 156.6, m 238-239 , pK 3.99. Same as for m-chlorobenzoic acid. Has also been crystd from hot water, and from EtOH. 

Case 2 - The Hyde Park Landfill site, located in an industrial complex in the extreme northwest corner of Niagara, New York, was used from 1953 to 1975 as a disposal site for an estimated 80,000 tons of chemical waste, including chlorinated hydrocarbons. A compacted clay cover was installed in 1978 over the landfill and a tile leachate collection system was installed in 1979. Hazardous compounds such as ortho-, meta- and para-chlorobenzoic acid toluene ortho- and meta-chlorotoluene 3,4-dichlorotoluene and 2,6-dichlorotoluene were detected in the leachate (Irvine et al., 1984). Since 1979, the existing leachate treatment system has used activated carbon as the technology for removing organic carbon. Although... 

The advantages of m-chloroperbenzoic acid have already been emphasized it is commercially available, stable and highly selective when methylene dichloride is used as solvent, the m-chlorobenzoic acid precipitates from solution, thereby decreasing the danger of acid-catalyzed side reactions." ... 

Esters of bomeol are obtained by the action of dry oxalic acid on turpentine under suitable conditions. From these, borneol is obtained by saponification and is oxidised to camphor. Some other acids produce a similar result, as, for example, salicylic and chlorobenzoic acids. 

Chlorobenzene, electrostatic potential map of, 565 13C NMR absorptions of, 536 phenol from, 575 p-Chlorobenzoic acid, pKa of, 760... 

Phenoxthin has been obtained by a series of reactions utilizing thiocatechol and 3,5-dinitro-4-chlorobenzoic acid 1 as the starting materials, from phenoxtellurin and sulfur,2 and by the action of sulfur and aluminum chloride upon phenyl ether.3... 

Dibromoethane, 1-bromononane (98%), 4-chlorobenzoic acid methyl ester (99%), and Fe(acac)3 (99.9%) were purchased from Aldrich Chemical Co. and used as received. 

The pyrolysis of vinylidene chloride produced a range of chlorinated aromatic compounds including polychlorinated benzenes, styrenes, and naphthalenes (Yasahura and Morita 1988), and a series of chlorinated acids including chlorobenzoic acids has been identified in emissions from a municipal incinerator (Mowrer and Nordin 1987). 

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. 

The diuretic clopamide (35) is synthesized from p-chlorobenzoic acid (33) by chlorosulfonation and subsequent ammonia treatment to give 34. This is converted to its acid chloride with thionyl chloride and reacted with the desired hydrazine derivative... 

Care must be taken to use pure o-chlorotoluene in this preparation otherwise the o-chlorobenzoic acid may be contaminated with isomeric acids which are very difhcult to remove. The o-chlorotoluene therefore should be prepared from pure o-toluidine or o-chlorotoluenesulfonic acid. 

Recoveries of halogenated organics range from 92% (1,2 dibromoethane) to 105% (m-chlorobenzoic acid). 

In both the Ni(acac)2-[bmim][PF6] and fhtorous biphasic systems, catalyst leaching is very low and several further batch oxidation reactions may be carried out with similar results to those obtained in the first run. In the fluorous biphasic system, the yield of 4-chlorobenzoic acid dropped from 87 % to 70 % by the sixth reaction cycle using [bmim][PF6] as a solvent, the yield was essentially the same after four uses, and no catalyst was found to leach into the organic phase. 

CASRN 118-91-2 molecular formula C7H5CIO2 FW 156.57 Biological. Suflita et al. (1982) reported that 2-chlorobenzoic acid degraded under anaerobic conditions by a stable methanogenic bacterial consortium enriched from sludge. The primary... 

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