TRANSACTIONS OF SECTION B. 689 
the free acid, especially as the production of tartronic acid has been much simpli- 
fied.1 This transformation has not hitherto been effected, although the converse 
operation—the reduction of mesoxalic to tartronie acid—is well known. 
Lactic acid, in a similar manner, yields pyruvic acid, but the operation requires 
especial care. 
Glyceric acid, when oxidised in the same way, produces a substance having 
strong reducing properties, and which gives an intense violet colour with ferric 
salts in the presence of alkalis. On treatment with phenylhydrazine acetate an 
osazone is produced which crystallises in golden needles, melts at 203°, and gives 
a beautifully crystalline sodium salt and pyrazolon. It appears to coincide in every 
way with the osazone of oxypyruvic acid C,,H,,N,O,, which was obtained by 
Nastvogel from dibrompyruvic acid,’ and by W. Will from the product of the 
action of soda on collodion wool.? The substance produced in the present case 
may therefore be (1) oxypyruvic acid, (2) the semi-aldehyde of tartronic acid or 
(8) the semi-aldehyde of mesoxalic acid. 
Malic acid—Judging from previous results, it was to be expected that this 
substance would yield oxal-acetic acid, and it is possible that such may be the 
result in the first instance, since, on treatment of the product with sulphuric acid, 
a certain amount of pyruvic acid is obtained. If, on the other hand, the product 
be treated with phenylhydrazine acetate, a substance is obtained which crystallises 
= golden prisms, melts at. 216°-218°, and gives crystalline sodium and potassium 
ts. 
The above-mentioned products are being fully investigated, and the results will 
shortly be published. 4 
The author wishes to express his thanks to Mr. H. O. Jones, B.Sc., for the 
valuable assistance which he is giving in this portion of the work. 
7. Condensation of Glycollic Aldehyde. By Henry J. Horstman FENTON, 
M.A., F.R.S., and Henry Jackson, B.A., B.Sc. 
It has been pointed out by one of the authors in previous communications that 
tartaric acid, when oxidised in presence of a small quantity of ferrous iron, gives 
rise to dioxymaleic acid, C,H,O,; and that this acid readily decomposes in 
aqueous solution, giving glycollic aldehyde, C,H,O,. This aldehyde has recently 
been isolated by the present authors in a crystalline state. It was further shown * 
that glycollic aldehyde, when heated to 100°-105° under reduced pressure, under- 
goes polymerisation, giving rise to a true hexose, C,H,,O,. The condensation 
effected in this way is not complete, and the resulting product has to be purified 
from the unaltered glycollic aldehyde by treatment with absolute alcohol; the 
yield of the sugar is consequently small, so that further study of its nature was 
extremely difficult. 
_ The-authors have therefore sought to modify the method of production with a 
view to increasing the yield, and have studied the results of effecting the conden- 
sation (1) at higher temperatures; (2) under the influence of alkalis. 
If the aldehyde be heated to about 130°-140° for a short time, a substance is 
- obtained which dissolves easily in water, but is precipitated as a brownish-white 
powder on addition of alcohol; whereas at a temperature of about 160°-170° a 
brown spongy substance is formed, which is nearly insoluble in boiling water, and 
on analysis its composition is found to be approximately C,H,,0.. 
When an aqueous solution of the aldehyde is mixed with a dilute (1 per cent.) 
solution of caustic soda, it begins to turn brown almost immediately. After 
_ standing for about twenty-four hours at the ordinary temperature (about 15°), the 
mixture no longer reduces Fehling’s solution in the cold, nor answers Schiffs 
aldehyde reaction with magenta, The solution now gives with phenylhydrazine a 
precipitate consisting of clusters of bright yellow needles, which melt at 158° and 
1 Trams. Chem. Soe. 1898, 72. 2 Annalen, 248, 85. 8 Ber. 1891, 400. 
4 J. C. 8. Trans. 1899, p. 575. 5 Fenton, ibid. 1897, p. 375. 
1899, vy 
