Of 2-hydroxy-6-methylbenzoic acid

From the beginning It was feasible that the formation of the salicylic moiety in the Ci5 series was likely to be similar to that of 2-hydroxy-6-methylbenzoic acid (6-methylsalicylic acid) in Penicillium grisofuMum (ref.86) although, remarkably, the interesting case of Anacardium occidentale found no mention in one account (ref. 

Other routes to the parent orsellinic acid have been listed (ref. 119). Cycloaromatisation reactions have been employed for the synthesis of 2-hydroxy-6-methylbenzoic acid and for the 4-methyl isomer as shown in the scheme The syntheses which are claimed to be regiospecific involve two different pathways in the reaction of 4-methoxybut-3-en-2-one with the bis-trimethylsilyl ether of 1-methoxybuta-1,3-diene, dependent on the conditions used (ref. 120). 

Collie s hypothesis that aromatic compounds are made biologically from ethanoic acid was greatly expanded by A. J. Birch to include an extraordinary number of diverse compounds. The generic name acetogenin has been suggested as a convenient classification for ethanoate (acetate)-derived natural products, but the name polyketides also is used. Naturally occurring aromatic compounds and quinones are largely made in this way. An example is 2-hydroxy-6-methylbenzoic acid formed as a metabolite of the mold Penicillium urticae ... 

Degradation procedures analogeus to those used for mycobactin P (see above) showed the aromatic residue to be salicylic acid (2-hydroxy-6-methylbenzoic acid in mycobactin P) and the hydroxy acid to be (+)-( -hydroxybutyric acid ((-)-3-hydroxy-2-methylpentanoic acid in mycobactin P). Fatty acid side chains substantially different from those in mycobactin P a minor component contains a s-octadec-2-enoic acid (identical to the principal product in mycobactin P). The major substituents in the fatty acid side chain are Cis to C21 fragments of unknown constitution. 

As a typical example of tridepside synthesis, the preparation of 5-0-methylhiascic acid (227) is depicted in Scheme 35 122). Persulfate oxidation of ethyl 4-benzyloxy-2-hydroxy-6-methylbenzoate (273) in potassium hydroxide solution gave the corresponding 5-hydroxy derivative (274) from which 2,4-dibenzyloxy-5-methoxy-6-methylbenzoic acid (275) was prepared. Condensation of this acid with benzyl lecanorate (276) gave the... 

Technically important dyes are salicylic acid derivatives that function as chrome mordant dyes for wool. Thus Cl Mordant Blue 1 (6.187) is made by the aldehyde synthesis from 2,6-dichlorobenzaldehyde and 2-hydroxy-3-methylbenzoic (o-cresotinic) acid in concentrated sulphuric acid. Oxidation of the leuco base is achieved by the addition of sodium nitrite. On wool the product, which is isolated as the sodium salt, is a dull maroon colour, changing to a bright blue on treatment with a chromium salt. Some dyes of this type, such as Cl Mordant Violet 1 (6.188), also contain a basic group. This compound is also prepared by the aldehyde route. 

Sparassol. 2-Hydroxy-4-methoxy-6-methylbenzoic acid methyl ester 4-methoxy-2,6-cresotic acid methyl ester everninic acid methyl ester orseJJinic acid methyl ester 4-methyl ether. CMH1204 mol wt 196.20. C 61.21%, H 6.17%, O 32.62%. Antibiotic substance produced by the fungus Sparassis ramose Falck, Ber. 56, 2555 (1923). Also obtained in methanol extracts of the lichen Evernla prunasti-Stenhouse, Ann. 68, 55 (1848) Spath, Jeschki, Ber. 57, 471 (1924). Structure Fischer. Hoesch, Ann. 391, 347 (1912) Wedekind. Fleischer, Ber. 56, 2556 (1923). Synthesis <3. Nicollier el at. Helv. Chim. Acta 61, 2899 (1978). 

A. Salicylates - The prominence given to the hazards associated with aspirin and phenacetin lends encouragement to the search for superior compounds. Tlie n-hexylcarbonate of salicylic acid50 is claimed to have activity equal to that of aspirin but with no ulcerogenicity. 2-Hydroxy-3-isobutyl-6-methylbenzoic acid is superior5 to aspirin as an analgesic. 

Needles (MeOH-H O), mp 163-164 °C React FeClj (EtOH) red, PD yellow Deriv Methyl 2-methoxy-4-hydroxy-5-formyl-6-methylbenzoate, needles, mp 135 °C (EtOH), from 2-methoxy-4-hydroxy-5-formyl-6-methylbenzoic acid with the calculated amount of CHjNj in EtjO at 0°C... 

Hydroxy-4-0-methylgyrophoric acid 183 183-184 By condensation of 2,3-dibenzyloxy-4-methoxy-6-methylbenzoic acid and benzyl lecanorate with TFAA and subsequent debenzylation (223)... 

By condensation of 2,4-dibenzyloxy-6-methylbenzoic acid and benzyl 4-benzyloxy-3-(2, 4 -dihydroxy-6 -methyl-benzoyloxy)-6-hydroxy-2-methylbenzoate with TFAA and subsequent debenzylation From 4-benzyloxy-2-hydroxy-6-/i-pentylbenzoic acid and olivetol with DCCD and subsequent debenzylation From 2-hydroxy-4-methoxy-6-n-propyl-benzoic acid and divarol with DCCD From 2-hydroxy-4-methoxy-6-n-propyl-henzoic acid and 3-methoxy-5-n-propylphenol with DCCD From 4-benzyloxy-2-hydroxy-6-n-pentyl-benzoic acid and 3-methoxy-5-n-propylphenol with DCCD and subsequent debenzylation... 

The co-condensation of 4 -acetylphenol-2,4-dinitrophenylhydrazone and substituted aminobenzoic acids such as2-aminobenzoic acid or acetyloxy-benzoic acid with methanal occurs under acid catalysis. But, the co-condensation of 4 -acetylphenol-2,4-dinitrophenylhydrazone, methanal, and any of the following benzoic acids 3-methylbenzoic acid, 4-aminobenzoic acid, and 2-(6-hydroxy-3-oxo-3H- xanthen-9-yl)-benzoic acid (phenolphthalein), occurs under base catalyst. These products generally have lower decomposition temperatures than those containing 3-(8 -pentadecenyl)phenol. 

Blaser D, Stdckli-Evans H (1992) Structure of the Methyl Ester of Eveminic Acid (Methyl 2-Hydroxy-4-methoxy-6-methylbenzoate). Acta Cryst C 48 1124 Bol L, Zhongwan L, Handong S (1990) Chemical Constituents from Lobaria isidiophora. Acta Bot Yunnan 12 447... 

Hydroxybenzo[6]thiophene has been isolated from coal tar.42 It may be prepared from 6-aminobenzo[fr]thiophene by standard procedures.241 6-Methoxybenzo[h]thiophene may be prepared by decarboxylation of the corresponding 2-carboxylic acid,341 and 6-ethoxybenzo[6]thiophene is obtained by reduction of 6-(ethoxy)-thioindoxyl (Section VI, 1,2). 6-Methoxy-5-methylbenzo[6]thiophene is obtained by cyclization of (3-methoxy-4-methylphenylthio)-acetaldehyde dimethyl acetal (Section IV,B).617 The product previously described542 as 6-hydroxy-3-phenylbenzo[6]thiophene has now been shown to be the 2-phenyl isomer.307 6-Methoxy-818 and 6-methoxy-5-methyl-benzo[6]thiophene617 are demethylated by pyridine hydrochloride. 

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