EUDESMIN AND ITS DERIVATIVES. 457 
ever prevented by the addition of veratrol and the colour 
obtained is then intense crimson lake. It is interesting to 
notice that a similar colour is produced when veratrol and 
glucose or cellulose are treated with concentrated sulphuric 
acid. With nitric acid eudesmin gives a pure yellow solu- 
tion, from which, in course of time, a nitro derivative 
(dinitro. eudesmin, see below) separates in crystals. Since 
aromadendrin gives in nitric acid a fleeting green and then 
a red solution the progress of a separation of eudesmin and 
aromadendrin may be easily followed. 
Eudesmin is unchanged by boiling alcoholic potash, by 
hydroxylamine, hydrazine and phenylhydrazine, and by 
semicarbazide in dilute acetic acid solution. It is also 
inactive towards acetylchloride, benzoyl chloride, phenyl 
isocyanate, and was recovered unchanged after being boiled 
during an hour with acetic anhydride and sodium acetate. 
It is clear, therefore, that it contains neither carbonyl nor 
hydroxy]. With an ethereal solution of magnesium methyl 
iodide a colourless precipitate is formed, but a few experi- 
ments showed that this isa common property of phenol 
ethers, and, for example, tetramethoxydihydroanthracene 
exhibits it almost in identically the same manner as eudes- 
min. It is more difficult to determine directly whether or 
not eudesmin contains ethylene linkages. It reduces 
potassium permanganate slowly in acetone solution, and is 
quickly attacked by bromine, but the reaction is one of 
substitution, and is accompanied by the production of 
hydrobromic acid, however little bromine is employed. The 
substitution derivatives described below are quite stable 
towards halogens, and eudesmin must, therefore, be satur- 
ated. Confirmation of this conclusion is obtained by study- 
ing the reduction of the substance since it was found that 
endesmin is unchanged after treatment witha great excess 
ofsodium amalgam in aqueous alcoholic solution, as also 
