CRYSTALLINE DEPOSIT OCCURRING IN TIMBER. 191 



slide cover glass, to float this on mercury, and to observe 

 the melting of the spangles with the aid of a lens. At 

 near the melting point the temperature was only allowed 

 to rise very slowly. 



The ready discoloration when bromine water was added 

 to the saturated aqueous solution, with the formation of 

 an insoluble bromide, indicated unsaturation, but this was 

 not confirmed by an alkaline solution of potassium perman- 

 ganate, as the colour of very dilute solutions remained 

 apparently unchanged for a considerable time, although 

 eventually oxidation to dimethylprotocatechuic acid took 

 place. There appeared to be no alteration on an attempted 

 reduction of the substance, when it was boiled with zinc 

 in an acetic acid solution. The formation of the bromide 

 was also found to have been by substitution, because when 

 bromine was added to a solution of the crystals in carbon 

 tetrachloride, hydrobromic acid was evolved in quantity. 

 Only one atom of bromine was introduced into the molecule 

 by this method, and this was in the side chain, as the 

 bromine was readily removed by boiling alcoholic silver 

 nitrate. The bromide was practically an amorphous body, 

 and attempts to crystallise it were not successful, nor did 

 it show a well defined melting point. 



One hydroxyl group was present in the side chain, but no 

 aldehydic group was formed even with mild reagents, the 

 oxidation to a carboxyl group being direct. The action of 

 concentrated halogen acids also indicated the presence of 

 an alcoholic OH group, and bromine was introduced into 

 the molecule when the substance was boiled in hydrobromic 

 acid. The molecule contains two methyoxy groups, and 

 the acid formed by oxidation was veratric acid. 



Neither an aldehyde nor carbonyl group was detected, 

 nor were indications for the presence of an ester or of a 

 glucoside obtained. 



