Ryan—On the Synthesis of Glucosides. 515 
recrystallized from water, dried at 105-110°, and melted at 163- 
165°. 
0:1406 gave 0:2966 CO, and 0:0894 H.O- C 57-53, H 7-06. 
C,; H,.O, requires C 57-77, H 6-66. 
(3 Orthocresylglucoside crystallizes from water in beautiful 
needles, scarcely soluble in ether, but easily so in water or alcohol, 
and does not reduce Fehling’s solutions before, but readily after, 
hydrolysis by dilute acids or emulsin. It has an intensely bitter 
taste. The yield of the orthoglucoside was similar in amount to 
that obtained from the para-derivative. 
Tetracetylorthocresylglucoside, C,H.,(C,.H;02),0 °O-C;H.C Hs, was 
obtained in the form of beautiful needles by heating a mixture 
of 1 gram orthocresylglucoside, 1 gram sodium acetate, and 4 c.c. 
acetic anhydride. The substance was isolated as in the case of the 
tetracetylnaphthylglucoside mentioned above. It was recrystal- 
lized from alcohol and dried at 105°; it melted at 143°. 
0:1752 gave 0°3687 CO, and 0:0945H,0, C 57-4, H 6. 
C.,H,,0,, requires C 57:5, H 5°8 per cent. 
It is soluble in ether, benzene, ethylic acetate, and chloroform, 
scarcely soluble in cold alcohol or water. Between crossed Nicols 
it is visible, and multi-coloured. Like tetracetyl 8/3 naphthyl 
and (3 p.-cresylglucoside, it is not acted on by emulsin. 
2 Metacresylglucoside, C,H1,0;°O°O,H,*CH:, was prepared 
from metacresol in a similar manner to that described for the 
ortho-compound. The yield was poorer than in the cases of ortho- 
and para-cresols. It crystallizes from 60 per cent. alcohol in fine 
branching needles, scarcely soluble in benzene, chloroform, ethylic 
acetate, or carbon bisulphide, soluble in cold water or alcohol, and 
readily soluble in hot water or alcohol. It reduces Fehling’s 
solution only after hydrolysis by dilute acids. It was dried at 
105° and melted at 167°5-168°5°. 
0:2004 gave 0:4239 CO, and 0:1181 H,O- C 57-63, H 6°55. 
C,sH,.O; requires C 57°77, H 6°66. 
From the above it would seem that the monosubstituted alkyl 
phenols react even more readily with acetochloroglucose than does 
phenol itself. 
