3.6- Dichloro-2-methoxy-benzoic acid

Zhao H, Jaynes WF, Vance GF (1996) Sorption of the ionizable organic compound, dicamba (3,6-dichloro-2-methoxy benzoic acid), by organoclays. Chemosphere 33 2089-2100... 

The most selective member of the benzoic acid herbicides is 3,6-dichloro-2-methoxy-benzoic acid (dicamba, 4), (Sterry, 1961 Velsicol Chemical Co., 1974). 

Synonyms Banex Banvel Banvel CST Banvel D Banvel herbicide Banvel II herbicide Banvel 4S Banvel 4WS Brush buster Compound B dicamba Dianate Dicambe 3,6-Dichloro-o-anisic acid 2,5-Dichloro-6-methoxybenzoic acid 3,6-Dichloro-2-methoxy-benzoic acid MDBA Mediben 2-Methoxy-3,6-dichlorobenzoic acid NA 2769 Velsicol compound R Velsicol 58-CS-ll. 

Dichloro-phenyl)-ethoxy]-4-methoxy-benzoic acid (0.29 mmol) dissolved in 2 ml DMF was treated with A-ethylmorpholine (1.16 mmol), 1 -pyridin-4-ylmethyl-piperazine (0.29 mmol), and 0-((cyano(ethoxycarbonyl)methylene)amino)-l, 1,3,3-tetramethyluronium tetrafluoroborate (0.3 mmol), then stirred 60 minutes at ambient temperature. The mixture was concentrated, then dissolved in CH2C12, washed three times with saturated NaHC03 solution, dried with Na2S04, and reconcentrated. The residue was purified by chromatography with silica gel using n-heptane/EtOAc, 1 1, then EtOAc, and finally EtOAc/methyl alcohol, 10 1, and 102 mg product isolated. MS ES+, m/z = 500 (M+)... 

Benzoic acid-3,6-dichloro-2-methoxy-2-ethoxy-l-methyl-2-oxoethyl ester [87214-73-1]... 

Benzoic acid, 3,6-dichloro-2-methoxy-, compd with 2-propanamine (T.1) Dicamba, isopropylamine sal Isopropylamine 3,6-dichloro-o-anisate Propanamine, 3,6xiichloro-2-methoxybenzoate. Registered by EPA as a herbicide. Albaugh Inc. BASF Corp. Monsanto Co. 

Preparation by hydrogenolysis of 2,2, 4-tris-(benzyloxy)-3,5,5 -trichloro-4 -methoxy-6,6 -di-methylbenzo-phenone (SM) in the presence of 10% Pd/C in ethyl acetate containing concentrated hydrochloric acid (5 drops) (>90%) [1339], SM was obtained by Friedel-Crafts acylation of 5-(benzyloxy)-2-chloro-3-methoxytoluene with 2,4-bis-(benzyloxy)-3,5-dichloro-6-methyl-benzoic acid in the presence of trifluoroacetic anhydride in refluxing ethylene dichloride for 5 h (42%). 

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