The Methyl Esters of 3 Hydroxyphthalic Acid. Selective Reduction of Monomethyl Phthalates with Lithium Aluminum Hydride英文电子书.pdfVIP

5092 E. L. ELIEL,A.W. BURGSTAHLER,11.E. KIVARDA N D L. HAEPELE Lol. Ti directly. It yielded 2.8 g. of $-dichlorobenzene, 0.5 g. of was refluxed with 60 g. of 10% sodium hydroxide for two chlorobenzene, 0.6 g. of orange crystalline material (not hours. The sodium salt was filtered, acidified with hydro- identified) and 2.0 g. of a,$-dichlorohydrocinnamonitrile. chloric acid and recrystallized twice from absolute ethanol. The petroleum ether insoluble material on vacuum distilla- The colorless needles (88:7c) melted at 249.5-250 .%4b tion gave 17.4 g. of orange oil, a,$-dichlorohydrocinnamo- nitrile, which boils a t 128-132 ( 5 mm.).3a The oil, 4.1 g., CAMBRIDGE,MASSACHUSETTS [COSrRIBUTION FROM THE CHEMICAL LABORArORIES O F THE UNIVERSITY OF NOTRE DAME] The Methyl Esters of 3-Hydroxyphthalic Acid. Selective Reduction of Monomethyl Phthalates with Lithium Aluminum Hydride R Y ERNESTL. ELIEL,A M.l BURGSTAHLER,~ ~ DONALD~ E. KIVARD~ AND~ LOUISHAEFELF RECEIVEDAPRIL 23, 1955 Reaction of %hydroxyphthalic anhydride with methanol gives the 1-and 2-methyl esters in about a 3 2 ratio. A method for reducing methyl phthalate to phthalide in good yield by means of lithium aluminum hydride is described. In connection with another problem we were in- OH OH terested in the monomethyl esters of 3-hydroxy- I co I phthalic acid. Treatment of the anhydride I with hot methanol gave material melting over a wide range from which the pure half-ester