-Ryan—On the Synthesis of Glucosides. 509 
From the monatomic phenols, glucosides could not be obtained 
in this way,! but again, in the case of the diatomic and triatomic 
phenols, complex condensation products were got which resembled 
somewhat the glucosides. Thus glucose combines with one or two 
molecules of resorcinol to form amorphous condensation products, 
hydrolysable by boiling diluteacids. Similar substances have been 
obtained from pyrogallol and orcinol’ and from phloroglucinol.® 
Not only is the method useful in the case of the hexoses glucose, 
mannose, galactose, fructose, and sorbinose, but also for the pen- 
toses arabinose and xylose. In the case ofthe dodecoses, methyl 
and ethyl lactosides appear to have been formed, but never satisfac- 
torily isolated.‘ Isomaltose was synthesised in this way by Emil 
Fischer.’ 
The naturally occurring glucosides helicin and methylarbutin 
were obtained synthetically by Michael® by the third method of 
forming glucosides. By utilizing the acetochloroglucose of Colley 
as parent-substance, Michael obtained from it, by the action of the 
potassium compound of salicylic aldehyde in alcoholic solution, the 
well crystallized glucoside helicin. The reaction had proceeded 
thus :— 
OK 
C.H,Cl(OC;H,0),:O + CHC + 40,H,OH 
CHO 
= 0,H,,0,;:0- C,H. CHO + 4CH;COOC.H; + KCl. 
Similar reactions were carried out by Michael with phenol, 
guaiacol and eugenol,’ and by Drouin with thymol and a napthtol.* 
I have obtained the three cresylglucosides, ( naphthyl and carva- 
erylglucosides from acetochloroglucose and the corresponding 
phenolic compounds in alkaline alcoholic solution. ‘The method is 
very troublesome and the yield of glucoside poor. The latter fact 
is possibly due to the nature of the acetochloroglucose used, which 
was not crystalline, and probably a mixture of the isomerides a 
and 6 chloroacetoglucose, which would give a mixture of a and 6 
glucosides, the latter of which only was isolated. This is confirmed 
1 Emil Fischer and Jennings, Ber. 27 (1894), p. 1358. * Ber. 23 (1890), p. 3687. 
2 Thid. 3 Councler, Ber. 28 (1895), p. 27. 6 Comptes Rendus, 89. p. 355. 
4Emil Fischer, Neue Zeitsch. f. Riibenzucker- 7 Amer. Chem. Jour. 6. p. 336. 
industrie, 31. p. 67. ® Bull. Soc. Chim. m1. 13. p. 5. 
