198 H. G. SMITH. 



0*087 gram KOH in the second. One hydroxyl group is- 

 thus iudicated, and as this is not phenolic it must be in the 

 side chain. 



Bromide. — The bromide was formed by the addition of 

 bromine water in excess to the saturated aqueous solution 

 of the pure crystals. It was light drab in colour and was 

 not distinctly crystalline. When well washed and purified 

 from either it melted at about 100°, darkening much at 

 about 90°, but the melting point was not sharp. 



Determination of the bromine gave the following results: 

 0*3435 gram gave 0*2114 gram AgBr. = 26*2 per cent^ 

 bromine. 0*1554 gram gave 0*0985 AgBr = 20*9 per cent, 

 bromine. CV,H 1;! Br0 4 contains 26*58 per cent, bromine. 

 One bromine atom had thus been introduced into the mole- 

 cule. When the bromide was boiled in alcoholic silver 

 nitrate, a precipitate quickly formed ; the metallic silver 

 was boiled out from this with dilute nitric acid, the residue 

 washed, dissolved in ammonia and precipitated again by 

 nitric acid. The bromine atom was thus shown to have 

 been introduced into the side chain. 



Oxidation. — The crystals were dissolved in glacial acetic 

 acid and chromic acid in the same solvent slowly added 

 until in excess. The oxidation commenced at once with the 

 evolution of heat, the flask was thus cooled under the tap. 

 A chromium salt, which appeared to be insoluble in glacial 

 acetic acid, continued to form until the reaction was com- 

 plete. This salt was filtered off through cloth, squeezed,, 

 and the solid cake thus obtained dissolved in water, in 

 which it was readily soluble. The solution was then acidi- 

 fied, extracted with ether, and after the removal of the 

 acetic acid a solid acid remained. This was dissolved in 

 dilute alkali, filtered, acidified and the solution extracted 

 with ether. The acid thus obtained was fairly soluble in 

 boiling water but precipitated again on cooling, so that it 



