( 78 ) 
under the influence of sunlight; in the dark the addition takes place 
very slowly and almost imperceptibly. 
Dr. Prey has tried in many ways, with sacrifice of much time 
but in vain, to prepare trioxybutyric acid from the dihalogen com- 
pounds starting with the dibromo-derivative. The replacement of the 
two Br (or 1) atoms by hydroxyl or by the residues of acetic or 
benzoic acid did not succeed : this is caused by the great unstability 
of the halogen derivatives which very readily lose HBr (or HI) and 
often break up with evolution of carbondioxide. 
Some experiments with the benzoylester of the dibromo-amide 
O CO CoH; 
Z 
CH,Br CHBr CH — CONH, 
which was prepared by direct action of benzoyl-chloride did not lead 
to any result. These efforts will however be repeated in different 
directions. 
The synthesis of trioxybutyrie acid finally succeeded by treating the 
amide with an alkaline-solution of potassium permanganate, which 
converted the 
CH, = CH—CHOH—CONH, 
directly into 
CH,OH — CHOH—CHOH COOH, 
which was isolated in the form of the brucinesalt; from the latter 
the crystallised lactone?) was obtained. 
The yield, however, is but very small. 
It appears from the study of Drs. VAN DER SLEEN?) and Prey 
that an unsaturated oxyacid, such as a-hydroxybutenoie acid, 
CH, CH.CHOH . COOH, 
is a very unstable substance capable of decomposing and breaking 
up in various directions. 
The investigation of this substance will be continued. 
1) Rurr. Ber. 32 3678. 
2) See following article. 
