622 DR E. A. LETTS ON THE ACTION OF IODACETIC AND OF 
it seemed to be of importance to study the action of bromacetic ethyl ether on 
sulphide of methyl, to ascertain whether it would behave as the iodacetic ether 
or as bromacetic acid, and form an addition product. 
Pure bromacetic ethyl ether was prepared by dissolving bromacetic acid in 
about twice the quantity of absolute alcohol required to form the ether, and 
then adding a quantity of oil of vitriol about equal in weight to the bromacetic 
acid taken. The mixture, after remaining for some time at rest, was thrown 
into a large excess of water, and the oily liquid which separated out washed 
with water and rectified. That portion which passed over from 159-162’ C. was 
employed for experiment,—the boiling point of pure bromacetic ethyl ether 
being 159° C, 
A preliminary experiment showed that a reaction occurred when the ether 
was mixed with sulphide of methyl, and that a solid product resulted. 
25 grms. of the ether were mixed with 30 grms. of sulphide of methyl 
(equimolecular quantities of the two substances require for 25 grms. of the 
ether less than 10 grms. of sulphide of methyl, so that the latter was in large 
excess). The two substances mixed to a clear liquid, which, however, in a 
few seconds began to grow cloudy ; oily drops gradually precipitated, and these 
increased in amount until more than a quarter of the whole was converted 
into a colourless heavy liquid, which remained as a distinct layer. After about 
an hour and a half an opaque colourless crystal appeared in this, and rapidly 
increased in size until in a few minutes the whole of the oily liquid was con- 
verted into a crystalline mass; and on allowing the mixture to remain undis- 
turbed for a night the supernatant liquid had almost solidified from the presence 
of crystals. 
These were detached from the flask in which the experiment had been made, 
washed six or seven times with sulphide of methyl, and then dried in vacuo. 
When dry, they consisted of beautiful white scales,—very thin, and having 
a mother-of-pearl lustre,—which were exceedingly hygroscopic. They were very 
soluble in alcohol, and could not be readily recrystallised from it. Heated, 
* Methyl-thioglycollic acid and its compounds have not, so far as I can ascertain, been previously 
prepared, though thioglycollie acid and the thioglycollates have been well studied. 
Carus (“ Ann. der Chem. u. Pharm.” exxiv. 43) obtained the acid for the first time by the 
action of sulphydrate of potassium on chloracetic acid. 
R. Sremens (“Berichte der Deutsch. Chem. Gesell.” vi. 689) prepared the acid by the action 
of reducing agents on the body having the formula 
COCl 
CHE Sco1cn 
Heintz (“ Ann. d. Chem. u. Pharm.” cxxxvi. 223) prepared the ethyl ether by the action of 
boiling dilute sulphuric acid on the ethyl ether of sulphocyanate of glycolyl— 
H,SCN CH,SH 
| + H,S0, + 2H,o = | + NH,HSO, + CO,. 
CO,C,H, CO,C,H; 

