Of 2-hydroxy-6-methylbenzoic

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... 

Obtained by reaction of ethyl 4-sec-butoxy-2-hydroxy-6-methylbenzoate with sodium methylsulfinylmethide [5586] according to [5587],... 

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. 

Preparation by treatment of methyl 2-hydroxy-6-methoxy-4-methylbenzoate (methyl mono-O-methyl-p-orsellinale) (m.p. 94-96°) with sodium methylsulfinyl-methide (SM) formed in situ. SM was obtained by action of sodium hydride (3 equiv) with DMSO (7 equiv) in benzene at 50° for 1 h. (78%) [5592]. 

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 structure of tornabeatin A 53 could be determined by means of 1-D and 2-D NMR, UV, IR, and MS spectroscopy <2004P2605>. The structure of isopestacin (3-(2,6-dihydroxyphenyl)-7-hydroxy-5-methylbenzo[c]-furan-l(3/f)-one) 54 has been derived by H and NMR spectroscopy and further confirmed by X-ray crystallography <2002P179>. 

Thus, irradiation of methyl 3-methoxy-l-methyl-4-oxocyclohexa-2,5-dienecarboxylate (11 a) in protic or aprotic solvents resulted in complex mixtures from which methyl 4-hydroxy-3-methoxy-2-methylbenzoate (12 a) was obtained in low yield ( 7%). The photoisomerization of 2-methylcyclohexa-2,5-dienone (11b) in methanol provided the corresponding phenol 12b in 41% yield. It has been shown that the formation of these phenols required the intermediacy of methyl 1 -methoxy-6-methyl- and 1,6-dimethyl-2-oxobicyclo[3.1.0]hex-3-enecarboxylates the latter has been isolated. Therefore, electron-releasing substituents at C2 of the cyclohexa-2,5-dienone systems facilitate formation of Cl-substituted bicyclo[3.1.0]hex-3-en-2-ones. ... 

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... 

Preparation by selective methyladon of 2,4 -di-hydroxy-2, 4,6 -trimethoxy-6-methylbenzo-phenone [1183], with dimethyl sulfate in the presence of potassium carbonate in refluxing acetone for 23 h (85%) [1184]. 

Obtained (poor yield) by photo-Fries rearrangement of 2,4-dichloro-5-hy-droxy-3-methylphenyl 2-hydroxy-4-methoxy-6-methylbenzoate in ethanol at 20° for 75 h (3%) [754]. 

Preparation by reaction of ethyl 2-hydroxy-4-methoxy-6-methylbenzoate (m.p. 73-74°) with sodium methyl-sulfinylmethide, itself obtained from DMSO and sodium hydride (85%) [5587]. 

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)... 

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