Ryan and Algar — Monianic Acid and its Derivatives. 103 



0'79 grm. of magnesium was added to 6-86 gim. of a-biomonaphthalene 

 dissolved in anhydrous ether, and 6 grms. of ethyl montanate introduced 

 when all the magnesium had disappeared. The crude product was freed from 

 naphthalene by distillation with steam, boiled with alcoholic potash and 

 extracted with petroleum ether. The extract was recrystallised from alcohol, 

 but did not melt sharply. It was then extracted with boiling methyl alcohol, 

 leaving behind a portion which was almost insoluble in hot methyl alcohol. 

 The soluble portion melted at from 51° to 53° 0. and was probably the cor- 

 responding ketone. The insoluble portion was recrystallised from alcohol and 

 melted at from 57° to 58° 0. The yield was about 35 per cent. 



0-2002 grm. of the latter substance gave 0-6358 grm. of CO^, and 0-2008 

 grm. of HjO, corresponding to carbon, 86-61 per cent., and hydrogen, 11-14 



per cent. The tertiary alcohol G-iT^a ■ C . OH requires: carbon, 86-93 per 



C,„H/ 



cent., and hydrogen, 10-65 per cent. 



The ketone OsTHgjCO . Ci^H, requires carbon 85-39 per cent, and 

 hydrogen 11-61 per cent. 



The portion which melts at from 57° to 58° C. appears therefore to be main'ly 

 the tertiary alcohol, containing a small percentage of ketone. Di-a-naphthyl- 

 heptacosyl carbinol is a white solid, which crystallises in curved needles, and 

 is soluble in cold chloroform, benzene, ether, or hot alcohol. It is soluble in 

 cold petroleum ether, somewhat soluble in cold acetone and almost insoluble 

 in cold alcohol. 



Montaiiyl Chloride, CjtHssCOCI. 



This preparation was first attempted by heating a mixture of phosphorus 

 trichloride and montanie acid on a water-bath for about au hour, care being 

 taken to prevent water-vapour having access to the mixture. Quantities were 

 taken in accordance with the equation : — 



6E . COOH + 4PCI3 = 6 K . COCl + P^Oo + 6HC1. 



The chloride was freed from phosphorus compounds by dissolving it in 

 petroleum ether, filtering, and evaporating off the ether. This method was 

 found to be unsatisfactory; and better results were obtained by the use of 

 phosphorus pentachloride, according to the equation : — 



E . COOH + PCI5 = R . COCl + POOI3 + HCl. 



8-13 grms. of montanie acid were mixed with 3-98 grms. of phosphorus 

 pentachloride in a dry round flask fitted with a dry reflux condenser. The 

 piixture was heated for an hour on an oil-bath at a temperature of 120°-130°C. 



