Methyl 2-chlorobenzoate

Benzoic acid, 3-chlora-, methyl ester Benzoic acid, m-chloro-, methyl ester m-Chlorobenzoic acid methyl ester EINECS 220-814-1 HSDB 5465 Methyl 3-chlorobenzoate. 

This procedure appears to be fairly general for the aroylation of /3-diketones to give 1,3,5-triketones. Using this method, the submitters2 have aroylated benzoylacetone with methyl benzoate (87%), methyl />-chlorobenzoate (78%), and ethyl nicotinate (69%). Also, acetylacetone has been monobenzoylated with methyl benzoate to form l-phenyl-l,3,5-hexanetrione in 75% yield or dibenzoylated with the same ester to form 1,7-diphenyl-... 

Other auxin-like herbicides (2,48) include the chlorobenzoic acids, eg, dicamba and chloramben, and miscellaneous compounds such as picloram, a substituted picolinic acid, and naptalam (see Table 1). Naptalam is not halogenated and is reported to function as an antiauxin, competitively blocking lAA action (199). TIBA is an antiauxin used in receptor site and other plant growth studies at the molecular level (201). Diclofop-methyl and diclofop are also potent, rapid inhibitors of auxin-stimulated response in monocots (93,94). Diclofop is reported to act as a proton ionophore, dissipating cell membrane potential and perturbing membrane functions. 

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],... 

Alkyl-1,4-dihydropyridines on reaction with peracids undergo either extensive decomposition or biomimetic oxidation to A-alkylpyridinum salts (98JOC10001). However, A-methoxycarbonyl derivatives of 1,4- and 1,2-dihydro-pyridines (74) and (8a) react with m-CPBA to give the methyl tmns-2- 2>-chlorobenzoyloxy)-3-hydroxy-1,2,3,4-tetrahydropyridine-l-carboxylate (75) and methyl rran.s-2-(3-chlorobenzoyloxy)-3-hydroxy-l,2,3,6-tetrahydropyridine-l-carboxylate (76) in 65% and 66% yield, respectively (nonbiomimetic oxidation). The reaction is related to the interaction of peracids with enol ethers and involves the initial formation of an aminoepoxide, which is opened in situ by m-chlorobenzoic acid regio- and stereoselectively (57JA3234, 93JA7593). 

Reduction with zinc dust in aqueous sulfuric acid gives 2-methyl-4-aminothiophenol (28) Condensation with 2-chlorobenzoic acid (Ullmann reaction) leads to 29, which can close to but one thiox-anthone (25) on treatment with sulfuric acid. Although this procedure is longer than the original, the yields are good and the sequence is regioselective. ... 

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)... 

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. 

CN 4-chlorobenzoic acid (4-butyl-3,5-dioxo-1,2-diphenyl-4-pyrazolidinyl)methyl ester... 

C14H14CI2N2O2 16390-18-4) see Indometacin 4-chlorobenzoic acid methyl ester (C8H7CIO2 1126-46-1) see Moclobemide 2-chlorobenzoic add potassium salt (C7H4CIICO2 16463-38-0) see Thiethylperazine... 

Treatment of methyl p-chlorobenzoate with an equivalent amount of commercial potassium silanolate 97 in abs. diethyl ether affords, after 4h, pure, anhydrous potassium p-chlorobenzoate in 84% yield and methoxytrimethylsilane 13 a. Trimethylsilyl trifluoroacetate reacts hkewise with sodium trimethylsilanolate 96 in THF to give sodium trifluoroacetate, in 98% yield, and hexamethyldisiloxane 7 [119] (Scheme 4.45). 

Methyl 4-chlorobenzoate (13.65 g, SOmmol) was added in one portion to a stirred slurry of potassium trimethylsilanolate 97 (10.26 g, 80 mmol) in 500 mb dry ether at ambient temperature, under N2. After 4h the white slurry is filtered under N2, washed with ether, and dried under a stream of N2 to afford 13.1 g (84%) analytically pure potassium 4-chlorobenzoate [119] (Scheme 4.62). 

Taeger K, H-J Knackmuss, E Schmidt (1988) Biodegradability of mixtures of chloro- and methyl- substituted aromatics simultaneous degradation of 3-chlorobenzoate and 3-methylbenzoate. Appl Microbiol Bio-technol 28 603-608. 

Regulatory position The definition of residues includes orbencarb and its metabolites, methyl 2-chlorobenzylsulfone (1) and 2-chlorobenzoic acid (II)... 

Diazomethane In a distillation flask equipped with an distillation funnel and a cooler, place a solution of 5 g of potassium hydroxide in 8mL of water and 25 mL of ethanol. Warm the distillation flask to 65 °C in a water-bath. Add a solution of 21.5g (0.1 mol) of A-methyl-lV-nitroso-p-toluenesulfamide in 130 mL of diethyl ether through the instillation funnel in 5 min. If the distillation funnel becomes empty, pour 20 mL of diethyl ether into the funnel, and distill it gradually. Continue distillation until the distilled ether solution becomes colorless. About 3 g of diazomethane is contained in the whole resultant ether distillate. Caution these procedures should be conducted in a laboratory hood Orbencarb, methyl 2-chlorobenzylsulfone (I), 2-chlorobenzoic acid (II), methyl 2-chlorobenzoate analytical standard materials (Ihara Chemical Industries Co., Ltd) Orbencarb and I standard solution for gas chromatography 1.0 qgmL in acetone Methyl 2-chlorobenzoate standard solution for gas chromatography 0.1 qgmL" in n-hexane... 

The intervention of an intermediate with the symmetry of a benzocyclopropenone (166, R = Cl) is also demanded by the formation of methyl p-chlorobenzoate in the photolysis of the lithio derivative 173 of the chlorosubstituted 3-p-tolylsulpho-nylamino-benzo-l,2,3-triazin-4-one128) ... 

Methamidophos, see Acephate Methane, see Acetaldehyde, Benzoic acid, 7 Bromobenzoic acid. 3-Bromobenzoic acid. 4-Bromobenzoic acid. Bromoform, Carbatyl, Catechol, 2-Chlorobenzoic acid. 3-Chlorobenzoic acid. Chloroform, Dibromochloromethane, 2,5-Dichlorobenzoic acid. 1,2-Dichloroethane, Ethylamine, Ethyl bromide. Ethylene dibromide, Ethylenimine, Formic acid, Hydroqninone, 4 Hvdroxvbenzoic acid. Indole, 2-Iodobenzoic acid. 3 lodobenzoic acid. Methyl bromide, 4-Iodobenzoic acid. 2-Methylphenol, 4-Methylphenol, Phenol, Prorocatechuic acid. Svringic acid. Svringaldehvde. TCDD, Tetrachloroethylene, Toluene, Trichloroethylene, Vanillin. Vanillic acid. Vinyl chloride... 

According to the other scheme, phenylhydrazone (3.2.46) undergoes cyclization in the presence of the same p-chlorobenzoic acid chloride, during which acylation of hydrazone and its cyclization into methyl ester of 5-methoxy-2-methyl-2-(p-chlorobenzoyl)-3-indoly-lacetic acid (3.2.52) simultaneously take place. The resultiug product is further hydrolyzed by au alkali to give indomethaciu (3.2.51) [113,114]. 

The second way differs from the first in that the methylation of nitrogen is accomphshed before the cyclocondensation reaction. In order to do this, the initial 2-amino-5-chlorobenzo-phenone is first tosylated by p-toluenesulfonylchloride and the obtained tosylate (5.1.3) transformed into the N-sodium salt, which is then alkylated by dimethylsulfate. The resulting 2-A -tosyl-A -methyl-5-chlorobenzophenone (5.1.4) is hydrolyzed in an acidic medium, giving 2-methylamino-5-chlorobenzophenone (5.1.5), which undergoes cyclocondensation by reaction with ethyl ester of glycine hydrochloride, forming the desired diazepam (5.1.2) [1-5]. 

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