SALICYLIC ACID. 345 



droxide (dissolved in alcohol), and 3-4 parts of methyl 

 iodide at 100-120, there is produced the liquid (boil 

 ing point, 248) methyl ether of methylsalicylic acid, 



C 6 H 4 i n(?o^QTj3 which when boiled with soda-ley 



yields sodium methylsalicylate ; from the solution of 

 this salt hydrochloric acid precipitates the free acid. 

 Large, colorless plates, difficultly soluble in cold water, 

 easily soluble in hot water and in alcohol ; fuses at 

 98.5, and above 200 is resolved into anisol (p. 291) 

 and carbonic anhydride. Strong monobasic acid. Its 

 salts are just as instable as the salicylates. 



Ethylsalicylic acid, C 6 II 4 j OOOH. Is obtained 



in the same way as methylsalicylic acid. Crystalline 

 mass ; fusing point, 19.5 ; is resolved into carbonic 

 anhydride and phenol-ethylether at 300. 



Acetylsalicylic acid, C 6 H 4 j C Q Q^- is produced 



by the action of acetyl chloride on salicylic acid or 

 salicylates. Colorless, fine prisms. 



Salicylamide (Salicylamic acid), 

 C 6 H 4 1 QQ -^jp (isomeric with the amidobenzoic acids) 



is produced by continued action of ammonia on gaul- 

 theria oil, and by heating ammonium salicylate. -Pale 

 yellow, crystalline laminae, difficultly soluble in water ; 

 fusing point, 142 ; sublimable. 



When salicylic acid is distilled with phosphorus 

 chloride, orthochlorbenzoyl chloride (p. 328) is pro 

 duced. Dry chlorine tranforms it, according as sali 

 cylic acid or chlorine is in excess, into chlorsalicylic acid, 

 C 7 H 5 C10 3 , or dichlorsalicylic add, C 7 H 4 CP0 3 ; bromine 

 also forms brom- or dibromsalicylic acid ; iodine in alka 

 line solution or in aqueous solution in the presence of 

 iodic acid converts it into a mixture of iodo-, diiodo- 

 and triiodosalicylic adds, which are difficult of separa 

 tion. All these acids crystallize well, and are but 



