Methyl 2-methoxy-4-hydroxy-6-methylbenzoate

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

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... 

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. ... 

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... 

Methyl 5-chloro-iso-everninate, Methyl 2-methoxy-4-hydroxy-5-chloro-6-methylbenzoate (5-Chlor-iso-everninsauremethylester, 2-Methoxy-4-hydroxy-5-chlorbenzoesauremethylester)... 

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... 

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). 

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). 

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]. 

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]. 

Methyl 3-methoxysalicylate. Methyl 2-hydroxy-3-methoxybenzoate, 1545 Methyl mono-O-methyl-p-orsellinate. Methyl 2-hydroxy-6-methoxy-4-methylbenzoate, 1547... 

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