Derivatives of salicylic acid. XIII. Chlorosalicylic acids and their methyl ethers was written by Hirwe, N. W.;Rana, K. N.;Gavankar, K. D.. And the article was included in Proceedings – Indian Academy of Sciences, Section A in 1938.Application In Synthesis of 5-Chloro-2-methoxybenzoic acid This article mentions the following:
3-Chlorosalicylic acid (I), m. 180-2°, is prepared by the action of Cl2 or nascent Cl (KMnO4 and concentrated HCl) on 5-sulfosalicylic acid (II) in glacial AcOH, followed by desulfonation with super-heated steam at 160-70°. The yield is 72% in the former case, from 100 g. II. A small amount of chlorophenol is probably also obtained in each case. I gives an intense violet color with FeCl3. Cl2 passed into chloralsalicylamide in glacial AcOH below 15° gives chloral-3-chlorosalicylamide (III), m. 159-60°, gives a red color with alc. FeCl3. III (20 g.) refluxed with 10% NaOH (200 cc.) for 6 h. gives I in 86% yield. K salt of I, needles from water; Ca salt contains 3H2O; Ag salt is light sensitive. Me 3-chlorosalicylate and aqueous NH3 give 3-chlorosalicylamide (IV), m. 174-5°, gives a violet-red color with FeCl3. I (10 g.) and PCl5 (12 g.) when refluxed 4 h. in low-boiling petroleum ether, and the reaction mixture treated with aqueous NH3, give IV, m. 174-6°; yield 8.5 g. When 7 g. Cl2 is passed gradually into 14 g. salicylic acid in ice-cold glacial AcOH, 5-chlorosalicylic acid, m. 172-3°, giving a violet color with alc. FeCl3, is formed in 15 g. yield; when double the quantity of Cl2 was used, 3,5-dichlorosalicylic acid (V), m. 219-20°, giving a reddish violet color with alc. FeCl3, was formed in 16.5 g. yield. Ca salt of V, contains 4H2O. Me2SO4 (100 g.) added to 17 g. I in 75 cc. cold aqueous KOH (40 g. KOH in 150 cc. water) gave 16 g. of 3-chloro-2-methoxybenzoic acid (VI), m. 120-21°, giving no color with alc. FeCl3. The Na salt of VI is anhydrous; the Ba salt contains 4H2O, and the Ag salt darkens. VI treated with PCl5 and aqueous NH3 gives 3-chloro-2-methoxybenzamide, m. 99-100°, giving no color with alc. FeCl3. 2-MeOC6H4CO2H (14 g.) chlorinated in ice-cold glacial AcOH with 7 g. Cl2 gives 5-chloro-2-methoxybenzoic acid (VII), m. 80-1°, giving no color with alc. FeCl3, in 15.5 g. yield. The Ag salt of VII turns brownish. VII (6 g.) treated with PCl5 and aqueous NH3 gives 5-chloro-2-methoxybenzamide, m. 137-8°, giving no color with alc. FeCl3; yield, 5 g. 2-MeOC6H4CO2H acid (15 g.) chlorinated in glacial AcOH with 15 g. Cl2, yields 15 g. 3,5-dichloro-2-methoxybenzoic acid (VIII), m. 166-7°, giving no color with alc. FeCl3. The Na salt of VIII contains 2H2O; the Ba salt, 5H2O; the Ag salt turns gray. VIII (20 g.) treated with PCl5 and aqueous NH3 yields 19.5 g. 3,5-dichloro-2-methoxybenzamide, m. 152-3° giving no color with alc. FeCl3. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Application In Synthesis of 5-Chloro-2-methoxybenzoic acid).
5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Application In Synthesis of 5-Chloro-2-methoxybenzoic acid
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics