Methyl 2-methoxybenzoate

Cooling is continued. A solution of 8.31 g. (0.05 mole) of methyl anisate (methyl 4-methoxybenzoate) (Notes 7 and 8) in 100 ml. of anhydrous tetrahydrofuran is added to the stirred mixture during a 6-10-minute period, and the resulting mixture is then stirred for an additional 30 minutes (Note 9). At the end of this period, 300 ml. of aqueous 3N hydrochloric acid is added. The nitrogen-inlet tube is removed and replaced by a reflux condenser, and the dropping funnel is replaced by a ground-glass stopper. The ice bath is removed, and the mixture is heated under reflux for 1 hour. The flask is then cooled, and its contents are poured into a 2-1. Erlenmeyer flask, and solid sodium bicarbonate is added to the mixture until neutralization is complete (Note 10). 

Methylmagnesium bromide, 55, 63 Methyl maleate, 56, 63 Methyl mercaptan, 56, 73 Methyl 4-methoxybenzoate, 55, 40 Methyl 5-methyl-2-hexynoate, 55, 76 7V-Methyl-2-methylthiothiazolium iodide,... 

Condensation of aromatic methylesters such as methyl 4-methoxybenzoate 351 a or methyl 4-hydroxybenzoate 351b with excess sodium-HMDS 486 in a mixture of THF-l,3-dimethyl-imidazolin-2-one (DMEU) at 185 °C in a closed vessel affords 59 or 93% of 4-hydroxybenzonitrile 298 as well as 26% 352 with smooth cleavage of the aromatic methyl ether in 351a (Scheme 4.47). Methyl indole-3-carboxylate gives hkewise 3-cyanoindole in 81% yield [127] (cf. also ref [92] in section 4.3). 

Cyanoanisole adds in the same fashion to benzonitrile, methyl 4-methoxybenzoate to acrylonitrile [86], and 2-methyl-4-cyanoanisole to acryloni-... 

Bis[4-methoxyphenyl] tellurium, obtained from 4-methoxybenzene and tellurium tetrachloride and reduction of the resultant bis[4-methoxyphenyl] tellurium dichloride, was converted to methyl 4-methoxybenzoate in 99% yield1. Methyl benzoate was similarly obtained from diphenyl tellurium in yields higher than 90%. These reactions can be carried out with catalytic amounts of palladium(II) chloride when copper(II) chloride is used as an oxidant1. 

A mixture consisting of methyl 4-methoxybenzoate (7.47 mmol) and 4-methoxyphenylacetonitrile (6.79 mmol) dissolved in 15 ml THF was added to 20 ml 2.0 M lithium diisopropylamide at — 10°C, then gradually warmed to ambient temperature, and stirred overnight. It was then quenched with water and concentrated. The residue was recrystallized using isopropyl alcohol and the product isolated in 65% yield as a red-orange solid, mp = 213°C. 

The nature of the nonbasic portion of aphelandrine was determined in two different ways KMn04 oxidation of 181, followed by CH2N2 treatment afforded two esters methyl 4-methoxybenzoate (182) and dimethyl 4-meth-oxyisophthalate (183) (Scheme 33). Both compounds answer the question of the substitution pattern of the cinnamic acid units of aphelandrine. The mode of connection of the two cinnamic acid residues can be deduced from products of the hydrolysis of 180, which forms lactone 184. The structure of... 

Methyl 2-methoxybenzoate Methyl 3-methoxybenzoate Methyl 4-methoxybenzoate... 

Phenols can also be prepared by combining two reactions that you have seen previously Baeyer-Villiger oxidation and ester hydrolysis. Oxidation of p-methoxyacetophenone with trifluoroperoxyacetic acid gives 4-methoxyphenyl acetate as the major product and methyl 4-methoxybenzoate as the minor one. 

Synonyms p-Anisic acid, methyl ester Benzoic acid, 4-methoxy-, methyl ester Benzoic acid, p-methoxy-, methyl ester Methyl anisate Methyl 4-methoxybenzoate Methyl p-methoxybenzoate Classification Aromatic ester Empirical CgHio03... 

Methyl 2-methoxybenzoate. See Methyl o-methoxybenzoate Methyl o-anisate Methyl 4-methoxybenzoate. See Methyl p-anisate... 

A mixture of dimethyl succinate and K-ferf-butoxide in ferf-butanol added during 2.5 hrs. with stirring under Ng to l-keto-2-methyl-2-cyano-5-methyl-6-methoxytetralin, stirring continued 3 hrs., and allowed to stand overnight methyl 1 - oxo - 8 - methyl - 4,5 - (3 - methyl -4 - methoxybenzo) -A 3(9)-hydrindene-3-carboxylate. Y 81%. D. K. Banerjee et al.. Tetrahedron 20, 2487 (1964). 

Anisic acid methyl ester see Methyl 4-methoxybenzoate 100-66-3 Anisole see Methyl phenyl ether 105-13-5 4-Anisyl alcohol see 4-Methoxybenzyl alcohol 75-05-8 ANT see EthanenitrUe 7440-37-1 Argon... 

Metboxybenzoic acid metbyl ester see Methyl 4-methoxybenzoate 4-Metboxybenzyl alcobol syn. 4-Anisyl alcohol 2-Metboxyetbanol... 

Components 1. CgHio02> 4-Methoxybenzyl alcohol [105-13-5] 2. C9H10O3, Methyl 4-methoxybenzoate [121-98-2] ... 

Methyl methoxyacetate Methyl 2-methoxybenzoate Methyl 3-methoxybenzoate Methyl 4-methoxybenzoate Methyl 3-methoxy-2-(methylamino)benzoate... 

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