XXI. 
THE SYNTHESIS OF GLYCOSIDES: SOME DERIVATIVES 
OF XYLOSE. 
By HUGH RYAN, M.A., D.SC., F.R.U.I., AND 
GHORGE EBRILL, B.A., 
Catholic University School of Medicine, Dublin. 
[Read, Novemper 19; Received for Publication, Novemprr 22, 1907; 
Published, January 13, 1908.] 
In 1870 Colley’ obtained acetyl-chloro-glucose by the interaction 
of acetyl chloride and glucose in a sealed tube at the ordinary 
temperature; and by reacting on the alkaline derivatives of 
salicylic aldehyde, methyl-hydro-quinone, phenol, eugenol, and 
guaiacol with acetyl-chloro-glucose in alcoholic solution, Michael’ 
synthesized the corresponding glucosides. Using a similar reaction, 
Drouin® prepared the glucosides of thymol and a-naphthol. By 
the action of alcoholic potash on equi-molecular quantities of 
acetyl-chloro-glucose, the cresols, carvacrol, and B-naphthol, Ryan‘ 
prepared the glucosides of cresol, carvacrol, and 8-naphthol, which 
he afterwards converted into their tetracetyl derivatives.’ 
From acetyl chloride and galactose, Ryan and Mills® ob- 
tained acetyl-chloro-galactose, and converted it into a-naphthyl- 
galactoside. 
Koenigs and Knorr’ succeeded in obtaining a well-crystallized 
Me 
1Ann. Chim. Phys., 1870, iv., 21, p. 363. 
* Comptes Rendus, Ixxxix., p. 355. 
3 Bull. Soc. Chim., xiii. (3), p. 5. 
4 Jour. Chem. Soce., 1899, vol. Ixxv., p. 1054. 
5 Proc. Roy. Dublin Soc., 1901, vol. ix., p. 508. 
6 Ibid., p. 506. 
7Sitz. Bayr. Akad. der Wissensch., 1900, p. 103. 
SCIENT. PROC. R.D.S,, VOL. XI., NO. XXI. : 2K 
