Methyl anisate

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). 

Methyl anisate was obtained from Eastman Organic Chemicals. 

AMINES - MAINES, AROMATIC - ANILINE AND ITS DERIVATIVES] (Vol 2) Methyl anisate [121-98-2]... 

Eastman Kodak (Eastman grade) methyl anisate was used without further purification. 

The method described is that of Miles, Harris, and Hauser2 and is an improvement over the earlier procedure of Hauser and co-workers.3,4 In the earlier method the dianion of benzoylacetone, formed by the action of alkali amide in liquid ammonia, was treated with methyl anisate to yield 1 -(/>-methoxyphenyl)-5-phenyl-l,3,5-pentanetrione (61% based on the ester). This compo ir d has also been prepared by the base-catalyzed ring opening of 2 - f -mcthoxyphenyl) -6-phenyl -4 pyrone however, no yield is reported.5... 

Methoxytetralin, 46, 82 Methylamine, 46, 85 Methyl anisate, reaction with disodlo-benzoylacetone, 46, 58 Methyl benzenesulpinate, 46, 62... 

Benzoic acid, 4-methoxy-, methyl ester methyl anisate 172a, 174b, 1053, 3266 ... 

Geranyl formate 226 Isoamyl cinnamate 274 Methyl anisate... 

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