3G8 PROFESSOR A. CRUM BROWN AND DR JAMES WALKER ON THE 



fuming hydrobromic acid, but is attacked by it at higher temperatures, with the produc- 

 tion of ethyl bromide and another neutral substance. Ten grammes of the substance 

 C 14 H 26 4 were heated in a sealed tube, with an equal volume of hydrobromic acid (sp. gr. 

 17), for ten hours to 110° C. On cooling, two layers were observed in the tube : the 

 lower aqueous layer was of a light brown colour, the upper ethereal layer was dark brown 

 and was filled with crystals. The contents of the tube were neutralised with solid 

 caustic soda and distilled with steam. Bromide of ethyl distilled over first, and then an 

 oil which solidified in the condenser and in the receiver to an aggregate of crystals. 

 These crystals were collected, freed from some unattacked C 14 H 2G 4 , and recrystallised 

 from various solvents. The residue in the flask, after everything that could be volatilised 

 with steam had been removed, was acidulated with hydrochloric acid, and again subjected 

 to distillation with steam. We thus obtained a trace of a volatile organic acid in the 

 distillate, and ascertained that no considerable quantity of acid, not volatile with steam, 

 remained in the residue. 



The crystalline substance which formed the main part of the product is insoluble in 

 water, moderately soluble in ether, in cold alcohol, and in cold benzene, very soluble in 

 hot benzene, sparingly soluble in cold ligroin, pretty soluble in hot ligroin. It was 

 recrystallised from benzene, and, finally, several times from boiling ligroin. The sub- 

 stance is neutral, when cold it is odourless, when warmed has an odour exactly like that 

 of camphor. It fuses sharply at 84°*5 C, and solidifies on cooling to a brilliant, snow- 

 white mass of crystals. Analysis led to the formula C 12 H2o0 3 . 



I. 01342 gramme gave - 3341 gramme C0 2 and 01146 gramme H 2 0. 



II. 01683 gramme gave 04180 gramme C0 2 and 01436 gramme H 2 0. 



III. 01528 gramme gave 0'3796 gramme C0 2 and 01307 gramme H 2 0. 



ed for C 12 H 20 O 3 . 





Found. 







I. 



II. 



III. 



67-92 



6790 



67-75 



67-76 



9-43 



9-49 



9-48 



9-51 



c 



H 



Determinations of the molecular weight by the Raoult-Beckmann method confirmed 

 the formula C 12 H 2 o03, which corresponds to a molecular weight of 212. 



0'5 42 gramme substance, dissolved in 7"90 grammes alcohol, raised the boiling-point 

 0°*360, which gives a molecular weight of 219. 



- 540 gramme substance, dissolved in 1816 grammes of glacial acetic acid, lowered 

 the freezing-point of the latter 0°'530, giving a molecular weight of 214. 



The substance has therefore been derived from the body C u H 20 O 4 by the loss of the 

 elements of alcohol, and the action of hydrobromic acid may be represented by the equa- 

 tion : Ci 4 H 26 4 4- HBr = C 12 H 2 o0 3 4-C 2 H 5 Br + H i ,0. The substance C 12 H 20 O 3 is not at all, 

 or only to the slightest extent, attacked by bases. Boiled for a long time with moderately 

 strong sulphuric acid, it was partially charred, but not otherwise changed. This indiffer- 

 ence to powerful reagents is inconsistent with the otherwise not unlikely formula — 



