Methyl vanillate

Fagnou et al. reported the synthesis of mukonine (11) starting from methyl vanillate (644). This synthesis uses both a palladium(0)-catalyzed intermolecular direct arylation and an intramolecular cyclization reaction. Triflation of methyl vanillate (644) afforded the aryl triflate 645. Using a Buchwald-Flartwig amination protocol, the latter was subjected to direct arylation with 2-chloroaniline (646) to furnish the corresponding diarylamine 647. Finally, intramolecular cyclization of 647 afforded mukonine (11). To date, this is the best synthesis (three steps, 75% overall yield) available for mukonine based on commercially available methyl vanillate (644) (582) (Scheme 5.45). 

Cation radical cyclization can be performed (and accelerated significantly) under sonication. Thus, the reaction of methyl vanillate with phenyliodonium bis(acetate) is initiated by ultrasonic irradiation and gives rise to the corresponding oquinone monoketal, which is trapped by a series of furanes. Monoadducts are formed reactions can be conducted at room temperature and are essentially complete within 15-50 min (Avalos et al. 2000). 

Benzeneazoresorcinol Vanillin Vanillic acid1 Methyl vanillate levo-Ep inep hrine64 dexiro-Epinephrine 62... 

Figure 4.8. The GC/MS-EI (70eV) SCAN mode chromatogram of compounds formed by acid hydrolysis of a Raboso grape skins extract. Peak 1. frans-furanlinalool oxide peak 2. cfs-furanlinalool oxide I.S.l, internal standard (1-octanol) peak 3. (Z)-ocimenol peak 4. ( )-ocimenol peak 5. a-terpineol I.S.2, internal standard (1-decanol) peak 6. 2-exo-hydroxy-l,8-cineol peak 7. benzyl alcohol peak 8. P-phenylethanol peak 9. actinidols A peak 10. actinidols B peak 11. endiol peak 12. eugenol peak 13. vinylguaiacol peak 14. p-menthenediol I peak 15. 3-hydroxy-P-damascone peak 16. vanillin peak 17. methyl vanillate peak 18. 3-oxo-a-ionol peak 19. 3-hydroxy-7,8-dihydro-P-ionol peak 20. homovanillic alcohol peak 21. vomifoliol.

Hydroxy-3-methoxy-benzoic acid ethyl ester (ethyl vanillate) 4-Hydroxy-3-methoxy-benzoic acid ethyl ether (vanillyl ethyl ether) 4-Hydroxy-3-methoxy-benzoic acid methyl ester (methyl vanillate) 4-Hydroxy-3-methoxy-benzoic acid methyl ether (vanillyl methyl ether) 4-Methyl-2-(2 -methyl-l-propenyl)-phenol 4-Methyl-2,6-dimethoxyphenol (methylsyringol)... 

Thirteen acylcarbene haloaromatic tags were prepared with trivial chemistry starting from the condensation of the known aryloxyalcohols (Figure 5) with methyl vanillate, saponification, formation of the acyl chloride, and finally re-... 

Progress towards the synthesis of maytansoids has been made by three independent groups. Meyers group have described in previous publications approaches towards the synthesis of the northern , southern , and eastern regions of the macrolide system (Vol. 7, p. 311) now they have described the synthesis of the western zone by a facile conversion of methyl vanillate (38) into the chloro-aniline (39) (Scheme 3). Another route has been described culminating in a synthesis of the N-methyl-acetanilide (41) by six steps starting from... 

Voitl T, von Rohr PR (2010) Demonstration of a process for the ctmvCTsirai of kraft lignin into vanillin and methyl vanillate by acidic oxidation in aqueous methanol, fitd Eng Chem... 

Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester. See Methyl vanillate Benzoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl) cyclohexyl ester. See Menthyl salicylate... 

Vanillic acid, methyl ester. See Methyl vanillate... 

Methyl propionate 3-Methyl-5-propyl-2-cyclohexen-1-one Methyl propyl ketone Methyl tiglate Methyl p-toluate Methylundecanal dimethyl acetal Methyl 9-undecenoate Methyl 10-undecenoate Methyl valerate Methyl vanillate Musk ketone Musktibetene Myrcene Myrcenol Myrcenyl acetate Myristaldehyde Myrrh gum Myrtenol Myrtenyl acetate Myrtenyl formate Myrtle (Myrtus communis) extract Myrtle (Myrtus communis) oii P-Naphthyi isobutyl ether P-Naphthyl methyl ether Neral Nerol Neryl acetate Neryl butyrate Neryl formate Neryl isobutyrate Neryi isovaierate Neryi propionate Nona-2,4-dienai trans,trans-2,4-Nonadienal 2,6-Nonadien-1-ol... 

Butyloctanol ISOFOL 12 Jarcol I-12 223-472-1 2-Decenal 223-474-2 trans-2-Decenal 223-478-4 Neryl isovalerate 223-520-1 Ethyl pivalate 223-525-9 Methyl vanillate 223-589-8... 

Another recent study on polyester synthesis through thiol-ene reactions for preparation of monomers from fatty-acid derivatives was described by Pang and co-workers [16]. Authors adopted the same approach for preparing aliphatic diols and diester from 10-undecen-l-ol, methyl 10-undecenoate and thiols. In parallel, they prepared aromatic diesters from methyl vanillate and a series of thermoplastic polyesters were synthesised by polycondensation of the diols and diesters using conventional transesterification methods. These materials were obtained with Mn values of 12-27 kDa and T values of -13 to 13 °C. 

To a stirred an cooled (-78°) solution of diisopropylamine in THF under nitrogen was added 2 M n-butylUthium solution in hexane. After stirring the mixture for 30 min, o-toluic acid in THF was added dropwise, and the resulting deep red solution was stirred at -78° for 1 h. Thereupon, a solution of methyl vanillate in THF was added dropwise, and the temperature was gradually allowed to reach room temperature. The mixture was then poured on ice/2 N HCl (66%) [6254]. m.p. 166-168° [6254]. 

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