404 
PROFESSOR WYNDHAM R. DUNSTAN AND DR. THOMAS A. HENRY 
continued for some time, the liquid becomes considerabty discoloured owing to the 
further action of the acid upon the products of hydrolysis. In addition to prussic 
acid, a sugar and a substance soluble in ether are produced. 
Paraliydroxybenzcddehyde. 
About 2 grammes of the dhurrin were dissolved in 50 cub. centims. of distilled 
water, and to the solution 10 cub. centims. of dilute hydrochloric acid were added, and 
the mixture heated on the water-bath for 5 minutes. The liquid was then extracted 
with ether and the ethereal solution dried and distilled. The residue was a brownish 
oil which, on standing, solidified to a mass of rosettes of needles. The crystals were 
dissolved in a small quantity of hot water, the solution filtered to remove resin, and 
cooled, when the substance separated in almost colourless needles, which could be 
picked out from a small quantity of the brown resin still adhering to them. After a 
second recrystallisation the melting-point remained unchanged at 118°. The substance 
is soluble in hot water, alcohol and ether. In aqueous solutions ferric chloride 
produces a purple coloration, and bromine water a white precipitate, which becomes 
crystalline on standing ; phenylhydrazine produces an immediate crystalline precipitate. 
When heated in a dry test-tube the substance melts and sublimes in needles on the 
cooler parts of the tube; the vapour lias a pleasant aromatic odour. 
A combustion of the purified material, dried at 100°, gave the following results :—- 
•1267 gramme gave '3196 gramme CCA, 68 '7 per cent, carbon. 
•0529 ,, IUO, 5T3 ,, hydrogen. 
C 7 H 6 0 2 requires C 68’8, H 4"91. 
The substance has therefore the composition of parahydroxybenzaldehyde. 
Owing to the small amount of material available, the action of bromine on this 
compound could only he studied by the addition ot excess ot bromine water to dilute 
solutions of the substance, a method of investigation which, as the sequel shows, gave 
rise to rather unexpected results. Under these conditions an amorphous precipitate 
is formed which soon crystallises in colourless needles, forming after recrystallisation 
from alcohol felted masses of needles melting at 92°, and having all the properties of 
tribromphenol. 
When a saturated aqueous solution of phenylhydrazine is added to a similar solution 
of the substance, a crystalline hydrazone is immediately formed, which is insoluble in 
ether and chloroform but soluble in hot alcohol. By operating in dilute solutions, a 
well-crystallised product is obtained, melting at 178°. It crystallises from hot alcohol 
in white needles which, on drying at 100°, become slightly green. 
A combustion of the hydrazone gave the following result :— 
•1117 gramme gave C0 3 , ‘3018 gramme 73'6 per cent, carbon. 
ELO, "0613 ,, 6‘07 ,, hydrogen. 
C 6 H 4 (OH)CH:N-NHC 6 H 5 requires C 73‘52 H 5'6. 
