Benzoic Chloro

Prepare a mixture of 30 ml, of aniline, 8 g. of o-chloro-benzoic acid, 8 g. of anhydrous potassium carbonate and 0 4 g. of copper oxide in a 500 ml. round-bottomed flask fitted with an air-condenser, and then boil the mixture under reflux for 1 5 hours the mixture tends to foam during the earlier part of the heating owing to the evolution of carbon dioxide, and hence the large flask is used. When the heating has been completed, fit the flask with a steam-distillation head, and stcam-distil the crude product until all the excess of aniline has been removed. The residual solution now contains the potassium. V-phenylanthrani-late add ca. 2 g. of animal charcoal to this solution, boil for about 5 minutes, and filter hot. Add dilute hydrochloric acid (1 1 by volume) to the filtrate until no further precipitation occurs, and then cool in ice-water with stirring. Filter otT the. V-phcnylanthranilic acid at the pump, wash with water, drain and dry. Yield, 9-9 5 g. I he acid may be recrystallised from aqueous ethanol, or methylated spirit, with addition of charcoal if necessary, and is obtained as colourless crystals, m.p. 185-186°. 

Prepare p-chlorobenzoyl chloride by refluxing and stirring 78 g. of p-chloro-benzoic acid (Section IV,157) and 100 g. of redistilled thionyl chloride until solution is complete. Distil off the excess of thionyl chloride at atmospheric pressure and then the acid chloride under reduced pressure 70 g. of product, b.p. 119-120°/ 22 mm., m.p. 14-15°. are obtained. 

Chlotobenzoyl)-benzoic acid is nitrated in concentrated sulfuric acid, then reduction of the nitro group, ring closure, and hydrolysis occur simultaneously in concentrated sulfuric acid in the presence of a reducing agent and boric acid. Thus obtained cmde chloro pink is purified by selective precipitation from sulfuric acid in order to separate it from by-produced 2-amino-3-chloto-l-hydroxyanthtaquinone (24) (36). 

N-(4 Methoxyphenyl)-N-benzoyl-3-chloro-3-chloroantranlllc acid (4) 2 To ice cooled NaoEt (Irom 0 11 g Na and 10 mL ElOH) was added in rapid succession meltiyl 2 chloro 6 hydroxybenzoate 2 (0 86 g 4 7 mmol) and N (4 methoxyphenyl)benzimidyl chloride 1 (t 14 g 4 7 mmol) in EI2O (30 mL) The mixture was stirred vigorously and allowed to stand at rt tor 48 h The oily solid obtained alter evaporation was heated to 210 215°C lor 70 min under N2 The product was diluted with water (5 4 mL) ElOH (10 8 mL) and treated with 1 M NaOEt (5 4 mL) The mixture was relluxed lor 90 mm the solvent evaporated and the aqueous solution acldilied The dark oil was heated with NaOH (7 5 g) m EtOH (22 mL) Alter removal ol benzoic acid by exhaustive extraction with water the product was recrystallized Irom EtOH to give 0 36 g ol 4 (27 7%), mp 139 5 140 5°C... 

Chloro-3-nitro-5 Sulfamyl Benzoic Acid n-Butanol... 

Chloro-4-amino benzoic acid (3-Diethyl amino ethanol... 

Chemical Name 5-(aminosulfonvl)-4-chloro-2-[(2-furanylmethvl)amino] benzoic acid Common Name —... 

Chemical Name 2-[(7-Chloro-4-quinolinyl)amino] benzoic acid 2 3-dihydroxy-propyl ester Common Name Glycerylaminophenaquine Structural Formula ... 

N-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by condensing m-methyl-mercapto-aniline (BP 163° to 165°C/16 mm Hg) with the potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N-(m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating, and then distilling. 

An analogous reaction of 6-chloro-2-(chloroacetamido)benzoic acid in aqueous dimethylform-amide for two hours at 90"C gives 6-chloro-4,l-benzoxazepine-2,5(l//,3/f)-dione (2b). 

Benzoic m-Toluic (Benzoic acid, 3-methyl-] p-Toluic [Benzoic acid, 4-methyl-J 3,5-Dimcthylbcnzoic [Benzoic acid, 3,5-dimcthyl-] p-Chlorobenzoic [Benzoic acid, 4-chloro-] p-Bromobenzoic [Benzoic acid, 4-bromo-J Phthalic [ 1,2-Bcnzcncdicarboxylic acid] Toluene [Benzene, methyl-] (78) m-Xylene [Benzene, 1,3-dimethyl-] (82) />-Xylene [Benzene, 1,4-dimethyl-] (74) Mesitylene [Benzene, 1,3,5-trimethyl-] (82) p-Chlorotolueno [Benzene, l-ehloro-4-methyl-] (94) p-Bromotolucnc [Benzene, l-bromo-4-methyl-] (94) o-Xylene [Benzene, 1,2-dimethyl-] (64)... 

Benzoic acid, 2-benzoyl-, methyl ester [606-28-0,21204-864], 63 Benzoic acid, 4-bromo- [586-76-5], 86 Benzoic acid, 4-chloro- [74-11-3], 86 Benzoic acid, 2-[(diethylamino)carbonyl]-, methyl ester [2659344-2], 63 Benzoic acid, 2,4-dimethoxy- [91-52-1 ], 31 Benzoic acid, 3,4-dimethoxy- [93-07-2], 31 Benzoic acid, 3,4-dimethyl- [619-04-5], 31 Benzoic acid, 3,5-dimethyl- [499-06-9], 86 Benzoic acid, 4-hydroxy- [99-96-7], 60 Benzoic acid, 3-methyl- [99-04-7], 86 Benzoic acid, 4-methyl- [99-94-5], 86 Benzoic acid, 2,4,6-tnmethyl- [480-63-7],... 

Several authors studied the influence of substituents on activation parameters. Bad-dar et al.315 who studied the polyesterification of y-arylitaconic anhydrides and adds with 1,2-ethanediol found that in the non-catalyzed reaction a p-methoxy substituent decreases both the activation enthalpy and the entropy whereas an increase is observed with a p-chloro substituent. On the other hand, Huang et al., who studied the esterification of 2,2-dimethyl-l,3-propanediol with benzoic, butanedioic, hexanedioic, decanedioic and o-phthalic add found the same values since the activation enthalpy is 64 kJ mol-1 for the first reaction and 61 kJ mol-1 for the others. 

Benzene, 4-(l-methylethyl)-1-pentyl- [Benzene, 4-isopropyl-l-pentyl-] 55,10 Benzenecaiboperoxoic acid, 3-chloro- [Per-benzoic acid, m-chloro-], 55, 88... 

CN 2-t(7-chloro-4-quinolinyl)amino]benzoic acid 2,3-dihydroxypropyl ester... 

C7H4CI2O4S 2494-79-3) see Bumetanide Clopamide 2-[4-chloro-3-(chlorosulfonyl)benzoyl]benzoic acid (C 4HgCl20jS 68592-12-1) see Chlortalidone 4-chloro-5-(chlorosulfonyl)-2-hydroxybenzoic acid (C7H4CI2O5S 14665-31-7) see Xipamide 4-chloro-3-(chlorosulfonyl)-5-nitrobenzoic acid (C7H3CI2NOSS 22892-95-1) see Bumetanide 6(x-chlorocortisone... 

CidHigCINO 87844-82-4) see Bisoprolol 4 chloro-2-[(methylphenyIamino)suifonyl]benzoic acid methyl ester... 

Miguez CB, CW Greer, JM Ingram, RA MacLeod (1995) Uptake of benzoic acid and chloro-substituted benzoic acids by Alcaligenes denitrificans BRI 3010 and BRI 6011. Appl Environ Microbiol 61 4152-4159. 

Preparation of 2 -Chloro-6 -diethylamino-3 -methylfluoran (68d). A mixture of 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (0.1 mol), p-chloro-m-cresol (0.1 mol), and 85% sulfuric acid (150 g) was stirred at 110-120°C for 5 h, and poured into water (1500ml). The precipitate was filtered off, washed with water, and then refluxed with a mixture of toluene (500ml) and 5% aqueous sodium hydroxide (200ml) for 1 h. The toluene layer was then worked up in the same manner as above to give 2 -chloro-6 -diethylamino-3 -methylfluoran in 85% yield as a white powder, mp 235-236°C. 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

Oxidation of diphenyl or di-tert. butyl cyclopropenone with wi-chloro peroxy-benzoic acid207 proceeds via intermediates corresponding to a Bayer-Villiger-type mechanism 277/278) to unrearranged products (1,2-diketones) or rearranged products (ketones) depending on the reaction conditions. 

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