Ryan and Algar — Montanic Acid and its Derivatives. 99 



di-tolyl and the di-naphthyl compounds. The preparations form an interesting 

 illustration of the great range of the " Grignard reaction," successful results 

 having been obtained by us with an ester containing thii'ty carbon atoms in its 

 molecule. 



The various derivatives of montanic acid described in the experimental 

 part of this paper show very little variation in physical properties, the amide 

 being the only one which melts at a somewhat high temperature. The 

 melting-points of the tertiary alcohols differ only very slightly from one 

 another. 



EXPEKIMEXTAL PaET. 



Preparation of Esters. 

 Methyl Montanate, CavH^aCOOCHj. 



Five grms. of montanic acid were dissolved, in a round flask, in about 

 120 CCS. of boLling methyl alcohol. About 5 c.cs. of concentrated sulphuric 

 acid were added, drop by drop, to the hot solution until the ester began to 

 separate on the surface in an oily layer. A further 2 or 3 c.cs. of acid was 

 then added, and the mixture heated on the water-bath for half an hour. The 

 white cake of ester which formed on cooling was removed, washed with water, 

 and dissolved in chloroform. The solution was then dried over calcium 

 chloride, filtered, and the chloroform evaporated off. The ester was 

 recrystallised from ethyl alcohol and dried on a porous pad. 



As the ester was found to contain a trace of free acid, it was dissolved in 

 hot alcohol, the free acid exactly neutraHsed with alcoholic potash, and the 

 alcohol then driven off on the water-bath. The pure ester was separated from 

 the potassium montanate by extraction with petroleum ether. 



The yield was almost quantitative. 



0-2138 grm. of the ester gave 0-6198 grm. of CO, and 0-2539 grm. of H,0, 

 corresponding to carbon 79-06 per cent, and hydrogen 13-29 per cent. CogHj^Oj 

 requires carbon 79-35 per cent., hydrogen 13-33 per cent. 



Methyl montanate is a white waxy soUd melting at 66° C. It is soluble 

 in cold chloroform and benzene, but almost insoluble in cold alcohol, acetone, 

 acetic ester, ether, or petroleum ether. It dissolves readily in these solvents 

 on warming, and crystallises in long curved needles. 



Hthyl Montanate, CoTHsjCOOCsHi. 

 This ester was prepared in a manner similar to that described for the 

 methyl ester. A quantitative yield of the pure ester melting at 64°-65° C. 

 was obtained. 



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