— 149 — 



The methyl derivative was obtained by boiling the sodium salt with 

 methyl iodide in alcoholic solution. It melted at 103 and upon 

 analysis gave the following values: — 



1. 0,1505 g. subst: 0,3443 g. C0 2 , 0,0939 g. H 2 0. 



2. 0,1620 g. „ 0,3708 g. „ 0,1005 g. „ 



Found : Calculated for C n H 14 4 : 



C 62,37% 62,34% 62,86% 



H 6,77% 6,85% 6,67% 



A methoxyl determination gave the following values: — 



0,3965 g. subst: ^3576 g- Agl. 



Found : Calculated for (O C H 3 ) 3 : 



OCH 3 45,37% 44,30% 



Treated with bromine in a chloroform solution, the phenol forms 

 a bromide, C 10 H n O 4 Br, m. p. 187 . This combination crystallises from 

 hot alcohol in yellow crystals. The bromine determination gave 

 figures which agree with those theoretically required. 



1. 0,1581 g. subst: 0,1076 g. AgBr 



2. 0,1853 g. „ 0,1270 g. „ 



3. 0,1770 g. „ 0,1259 g. „ 



Found : Calculated for C 10 H u Br 4 : 



1 11 in 



28,96% 29,16% 3O,280/ 29,09% 



The preparation of an oxime from the phenol C 10 H 12 O 4 proved 

 the still remaining fourth oxygen atom of the phenol molecule to belong 

 to a CO -group. For this purpose the phenol was boiled for several 

 hours with hydroxylamine hydrochloride and alcoholic potash. The 

 oxime which separated when acid was added melted, when purified 

 by means of dilute alcohol, at 108 to no°. It is coloured dark-red 

 by ferric chloride. The results of combustion agree with the formula 

 C 10 H 13 O 4 N:- 



0,1532 g. subst: 0,3170 g. C0 2 , 0,0856 g. H 2 0. 

 0,1657 g. „ 9,75 cc. N (16 , 742 mm.). 



Found : Calculated for C 10 H 13 4 N : 



c 56,39% 56,87% 



H 6,20% 6,i6o/ 



N 6,60 <>/ 6,63 o/ 



Attempts to obtain a semicarbazone remained fruitless. 



From the above results it is evident that the body C 10 H 12 O 4 

 contains, in addition to two methoxyl groups, a ketone group, and a 



