Ryan—On the Synthesis of Glucosides. ell 
differs from the other glucosides of the series by its being more 
difficultly hydrolysable, by its great solubility in dilute alkali and 
reprecipitation by dilute acids or ammonium carbonate. Hence 
earvacrylglucoside contains an unchanged phenolic hydroxyl group, 
and has the formula :— 
esos (§) ee ee 
OGY UE | 
CHLOE =) OR OG = OO E2Sc. tr 
Onn Ee ore 
C ELC H 
6 \OH 7 
The acetochloroglucose has reacted with carvacrol with separa- 
tion of hydrochloric acid and formation of a substance for which 
there is no analogue in the whole range of organic chemistry. 
Although the generic formula of the new class of substances 
XY - OH is no longer included in that of the glucosides X- O X,, 
where X is a carbohydrate radicle, I have preferred to retain the 
name carvacryl glucoside for the body owing to its similarity in 
appearance, and its hydrolysis by dilute acids or emulsin to glucose 
and carvacrol. 
Preparation of Acetochloroglucose—The acetochloroglucose was 
prepared by Colley’s method' with some slight alterations which 
render the substance more easily accessible. Pure, crystallized, 
anhydrous glucose (18 grams), after passage through a fine sieve, 
was mixed with acetylchloride (39 grams) in a well-dried Volhard 
tube. The tube was cooled in a freezing mixture, sealed off at 
once, and shaken on a machine during 24-30 hours at the ordinary 
temperature. ‘The colourless solution was dissolved in chloroform, 
washed first with iced water, then with ice-cold sodium carbonate 
solution until freed from acid. The chloroform solution was 
separated, filtered, dried with calcium chloride, and, after evapora- 
tion in a vacuum, gave a colourless semi-solid mass of acetochloro- 
glucose. It contained 9 per cent. chlorine (Cale. 9°68 Cl). The 
yield was about 36 grams. 
It may be mentioned that attempts to prepare acetochloro- 
glucose in an open vessel protected from atmospheric moisture by 
a calcium chloride tube, were unsuccessful. When 20 mols. of 
acetylchloride were employed with 1 mol. of glucose, the prin- 
1 Ann. Chim. Phys., 1870, [1v], 21, p. 363. 
