2-Hydroxy-4-methoxy-6-methylbenzoic

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). 

Everninic acid, 2-Hydroxy-4-methoxy-6-methylbenzoic acid (Everninsaure, 2-Hydroxy-4-methoxy-6-methylbenzoesaure)... 

Methyl everninate, Methyl 2-hydroxy-4-methoxy-6-methylbenzoate... 

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]. 

Dioxocin. 2H,6H-l,5-Dioxocin [292-95-5], 74, 225-226, 235, 238 Dioxybenzone. 2,2 -Dihydroxy-4-methoxybenzophenone, 432 Disyringylmethane. 4,4 -Dihydroxy-3,3, 5,5 -tetramethoxydiphenylmethane, 450 Epichlorohydrin. l-Chloro-2,3-epoxypropane, 104 Ethylcellosolve. Cellosolve or 2-Ethoxyethanol, 13 Everninic acid. 2-Hydroxy-4-methoxy-6-methylbenzoic acid, 482-483 Exifone. 2,3,3, 4,4, 5 -Hexahydroxybenzophenone, 40,495-496,498, 575 9-Fluorenone. 9-Oxofluorene, 5, 57, 149,167, 280... 

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... 

Ethyl isoeverninate. Ethyl 2-methoxy-4-hydroxy-6-methylbenzoate... 

Methyl iso-eveminate. Methyl 2-methoxy-4-hydroxy-6-methylbenzoate (Iso-everninsaure-methylester, 2-Methoxy-4-hydroxy-6-methylbenzoesauremethylester)... 

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... 

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... 

This does not occur in the case of catalyst and reactants here described. With Bronsted-type catalysis, the reaction between the benzoyl cation, Ph-C" =0, and the hydroxy group in phenol is quicker than the electrophilic substitution in the ring. This hypothesis has been also confirmed by running the reaction between anisole and benzoic acid in this case the prevailing products were (4-methoxy)phenylmethanone (the product of para-C-benzoylation) and methylbenzoate (obtained by esterification between anisole and benzoic acid, with the co-production of phenol), with minor amounts of phenylbenzoate, phenol, 2-methylphenol and 4-methylphenol. Therefore, when the 0 atom is not available for the esterification due to the presence of the substituent, the direct C-acylation becomes the more favored reaction. 

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. 

Staggered configurations have also been observed for the tricarbonyl chromium complexes of phenanthrene 294, 295), 9,10-dihydro-phenanthrene 293, 295), anthracene 202), naphthalene 262), and 1-aminonaphthalene 58). The eclipsed configuration has been observed for the tricarbonyl complexes of anisole (57, 229), toluidine 60, 61), methylbenzoate (59), o-methoxyacetylbenzene, o-hydroxyacetylbenzene 101), 2-methoxy-[l-hydroxy-ethyl]benzene (99), and 2-methyl-[l-hydroxy-l-phenylpropyl]benzene (97). It is apparent that the orientation of the chromium tricarbonyl moiety is in many cases controlled by the substituents on the ring to which it is coordinated, and this has been attributed to mesomeric electron repulsion or withdrawal by the substituents 374). 

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. ... 

Methoxy-4-hydroxy-5-formyI-6-methylbenzoic acid (2-Methoxy-4-hydroxy-5-formyl-6-methylbenzoesame)... 

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... 

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