BENZENE SERIES. AROMATIC COMPOUNDS. 585 



low), and is mentioned here because it splits into glucose and salicylic alcohol, 

 C 6 H 4 .OH.CH 2 OH, when boiled with dilute acids: 



C 13 H 18 7 + H 2 = C 6 H 12 6 + C,H 8 O r 



Salicylic alcohol is converted by chromic acid into salicylic aldehyde, C 6 H< 

 OH.COH, which by further oxidation is converted into salicylic acid. 



Salicin forms white, silky, shining needles, which are soluble in less than an 

 equal weight of water, have a neutral reaction and a very bitter taste. 



Salicin sprinkled upon concentrated sulphuric acid produces a red color. 

 Boiled with very dilute hydrochloric acid for a few minutes, and this solution 

 nearly neutralized with sodium carbonate, a violet color is produced on the 

 addition of a drop of ferric chloride solution. 



Methyl salicylate, Methylis salicylas, CH 3 ,C 7 H 5 3 or C 6 H 4 (OH)COOCH S 



1 ". 2 = 150.92. Oil of wintergreen is chiefly methyl salicylate, a nearly color- 

 less liquid with a characteristic, strongly aromatic odor. It is made by the 

 method so extensively used in the manufacture of esters, viz., by heating of 

 salicylic acid with methyl alcohol in the presence of sulphuric acid. (See 

 above reaction 3 of salicylic acid, ) It is also found in many other volatile oils, 

 especially in oil of betula 



Phenyl salicylate, Salol, Phenylis salicylas, C 6 H 5 .C 7 H 5 O 3 or 

 C 6 H 4 (OH)COOC 6 H 5 1:2 = 212.47. This ester is a white, crystalline, 

 almost tasteless powder, which is nearly insoluble in water, readily 

 soluble in alcohol, ether, and benzol, and fuses at 42 C. (107.4 F.). 

 It is used as an antiseptic and antipyretic. 



Salol heated with potassium hydroxide solution causes its decom- 

 position into phenol, which can be recognized by its odor, and potas- 

 sium salicylate, from which crystalline salicylic acid will separate 

 upon supersaturating the liquid with hydrochloric acid. An excess 

 of bromine-water produces a white precipitate in an alcoholic solution 

 of salol. 



Salol is made by the action of suitable dehydrating agents upon a 

 mixture of phenol and salicylic acid : 



C 6 H 5 OH -f HC 7 H 5 3 = C 6 H 5 .C 7 H 5 3 + H 2 O. 



A more simple method for its manufacture consists in the heating 

 of salicylic acid between 220 and 230 C. (428 and 446 F.) in an 

 atmosphere of carbon dioxide, in a flask with a long, narrow neck. 

 The reaction is this : 



Anisic acid, O 6 H 4 <j^| (Para-methoxy-benzoic acid), is isomeric with 

 methyl salicylate, but, unlike the latter, it is not saponified when heated with 



