YLANG-YLii.NG OIL. 79 



the aqueous portion well shaken with ether and the ether several times shaken out 

 witli small amounts of water so as to separate the alcohols soluble in that 

 medium, the water being ahvays added to the original alkaline solution. The 

 latter was now distilled with steam and the distillate treated with benzoyl 

 chloride according to Baumann-Sehotten, 1.2 grams of methyl benzoate being 

 obtained in this manner. A slight excess of dilute sulphuric acid was now added 

 to the alkaline solution in the distilling flask and the whole was then extracted 

 with ether, the latter being shaken out with small portions of water to remove 

 acids soluble in that medium, these extracts being added to the aqueous por- 

 tions. This was now distilled with steam, the distillate on titration with 

 standard alkali showed 5.54 grams of volatile acids calculated as acetic. The 

 barium and silver salts of the acids were prepared from this distillate and 

 analysed. 



I. 0.6916 grams barium salt gave 0.6466 gram barium sulphate. 

 II. 0.5195 grams barium salt gave 0.4872 gram barium sulphate. 



„ . Calculated (per cent) for 



Found *^ ' 



(percent). Ba(C2H302):2HoO Ba(CH02)o 



I. Ba. 55.06 48.7 60.7 



II. Ba. 55.10 



I. 0.2065 grams silver salt gave 0.1897 gram AgCl 

 II. 0.2050 grams silver salt gave 0.1885 gram AgCl 



„ , Calculated (percent) for 



Found * 



(per cent) AgCoHaO. AgCHOc 



I. Ag. 69.1 64.6 70.58 



II. Ag. 69.1 



This aqueous solution of the acids reduces potassium permanganate at once, 

 and readily converts mercuric to mercurous chloride. These results, taken in 

 conjunction with the analytical data and the fact that it was impossible to 

 obtain a white silver salt, leave no doubt but that formic acid was present. 

 The figures obtained for the silver salt are naturally different from those for 

 the barium compound because of the slight reduction to metallic silver caused 

 by the formic acid. 



The etherial solution containing the acids not soluble in water was now 

 repeatedly extracted with small portions of a solution of sodium carbonate. In 

 this manner there Avere isolated 9.6 grams of solid acids having the appearance 

 of benzoic and giving a test for salicylic acid with ferric chloride. The benzoic 

 and salicylic acids were separated by conversion of the salicylic acid into the 

 very insoluble dibromsalicylic acid. 0.6 gram, melting at 221° (found, bromine, 

 57 per cent; calculated, 57.4 per cent) sufficient water being used to keep the 

 benzoic acid in solution.'' The remaining acid, after extraction and one crys- 

 tallization from ligroin was 7.7 grams of pure benzoic acid melting at 121° to 

 122°. After removing the acids, 0.9 gram of phenols having an odor i-esembling 

 that of isoeugenol and giving a green color with ferric chloride was isolated. 



A metho.xyl determination according to Zeisel gave the following numbers: 

 0.92 gram of oil gave 0.1405 gram silver iodide equivalent to 0.031 grams of CHj. 

 This would represent 0.99 per cent of the total oil or 0.66 grams CH,OH which 

 would give 2.02 per cent of the total oil as CH3OH. It would require 2.5 grams 



"Sharpe: Zlsch. f. An. Chem. (1893). 32, 107. 



