Cartwright, N. J. published the artcileSynthesis of γ-resorcylic acid (2,6-dihydroxybenzoic acid), HPLC of Formula: 36335-47-4, the publication is Journal of the Chemical Society (1952), 3499-502, database is CAplus.
Details are given of the preparation of 2,6-(MeO)2C6H3CO2H (I) in 14.8% yield from m-C6H4(NO2)2, 125 g. I and 400 g. AlCl3 in 3.5 l. C6H6, refluxed 2 hrs., give 95-8% 2,6-(HO)2C6H3CO2H (II), m. 160-3° (decomposition); some decarboxylation occurs in boiling PhMe and, to a smaller extent, in boiling H2O. 2,6-(HO)2C6H3Ac (III) (133 g.) with Me2SO4 and aqueous NaOH gives 127 g. 2,6-(MeO)2C6H3Ac (IV); 100 g. III with MeI and K2CO3 in Me2CO (refluxed 12 hrs.) gives 95 g. IV. Oxidation of IV with Na-OCl at 85° (1.5 hrs.) gives 97% I; if the excess NaOCl is not removed before acidification, there results some 3-chloro-2,6-dimethoxybenzoic acid (V), m. 132°; 2 g. V and AlCl3 in C6H6, refluxed 4 hrs., give 1.65 g. 3-chloro-2,6-dihydroxybenzoic acid, m. 193°, blue color with FeCl3. 2,6-(HO)2C6H3Me (50 g.) in NaOH, treated with Me2SO4 and heated 2 hrs. on the water bath, gives 57 g. 2,6-(MeO)2C6H3Me; oxidation with KMnO4 (1 hr. at 80°) gives 73% I. The preparation of II in 51% yield from 1.58 g. resorcinol bis(tetrahydro-2-pyranyl) ether and BuLi by the method of Parham and Anderson (C.A. 43, 2203h) is reported.
Journal of the Chemical Society published new progress about 36335-47-4. 36335-47-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Ether, name is 3-Chloro-2,6-dimethoxybenzoic acid, and the molecular formula is C9H9ClO4, HPLC of Formula: 36335-47-4.
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