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NOTES ON SCIENTIFIC RESEARCH. 107 
Hydroxycamphenilanic acid. On page 146 of our April Report of 1914, we mentioned 
the preparation of hydroxycamphenylanic acid, as described by S. V. Hintikka. In a 
paper published later on, Hintikka') reports fully on the production of this acid. He 
cautiously oxidizes camphene in aqueous acetone with potassium permanganate and 
removes the acetone, as well as the unaltered camphene and camphenilone by steam 
distillation.. After evaporating the solution and extracting it with ether, he purifies 
the acid by way of the sparingly soluble sodium salt. It melts at 182°. 
The 4 isomeric acids, Cy>HisCOoH, resulting when camphene and bornylene are 
oxidized’), have been converted into their methyl esters by G. G. Henderson and 
M. M. Sutherland’). They are viscid, colourless liquids, which all boil at about 103 
to 104° (22 mm.). The esters of camphenilanic, zsocamphenilanic and camphenanic 
‘ acids yield the corresponding acids when hydrolysed; however, on hydrolysis of the sup- 
posed ester of 7socamphenanic acid, a mixture of camphenilanic and zsocamphenilanic 
acids was obtained. It seems therefore that isocamphenanic acid consists of a mixture 
of camphenilanic and zsocamphenilanic acids, or that it is converted into these acids 
during the formation of the esters. | 
On being treated whith sodium and alcohol, each of these esters furnishes cam- 
phenilanol, C,His-CH.,OH, a crystalline mass, melting at 77°. Chromic acid mixture 
oxidizes camphenilanol to camphenilanaldehyde. The hydrogen phthalate of cam- 
phenilanol meits at 153°; the p-nitrobenzoate, at 90°. 
During the reduction of each of the esters, small quantities of zsocamphenilanic 
acid are formed. Camphenilanic and camphenanic acids may therefore in this way be 
transformed into zsocamphenilanic acid. 
- Pinie acid. When reducing pinic and norpinic acids according to Bouveault and 
Blanc, J. Ostling*) obtained the corresponding glycols, boiling at 166 to 167° (16 mm.) 
and 138 to 140° (15 mm), respectively. They afforded dibromides melting at 144 to 145° 
(10 mm.) and 126 to 128° (10 mm.), respectively. Dimethyl and diethyl d-camphorate 
which had been prepared by means of methyl and ethyl sulphate, were likewise reduced, 
when a glycol (b. p. 158 to 160° at 16 mm.) and a hydroxy acid were formed, the 
methyl ester of which boiled between 145 and 146° (14 mm.). 
Ascaridolic acid. The resolution of 7-ascaridolic acid®) was carried out by E. K. 
Nelson’). He found that the cinchonidine salt of the dextro-rotatory modification is 
less readily soluble in hot water than that of the laevogyrous one, so that it is easy to 
Separate the two salts from each other. The d-acid shows [@]pu0-+13,93° (8,218 p.c. 
solution in chloroform); the J-acid, [¢]px0—13,77° (8,172 p.c. solution in chloroform). 
Both acids melted at 129 to 130°; the inactive acid melts at 117°. 
Cyanolauronic acid. W.Borsche and W. Sander’) tried to prepare the chloride of 
cyanolauronic acid by distilling isonitrosocamphor with phosphorus pentachloride; 
however, no pure product resulted, but a mixture of chloride and of nitrile of campho- 
ceenic acid. In order to prepare pure chloride, the authors started from pure cyano- 
1) Ann. Accd. Scient. Fennicae A. 5 (1914), No. 3. From a reprint kindly sent us. — 2) Comp. Report 
October 1911, 134; April 1912, 170; April 1914, 130. — #*) Proceed. chem. Soc. 80 (1914), 203. — *) Chem. 
Ztg. 38 (1914), 944. — *) Comp. Report October 1911, 114. — *) Journ. Americ. chem. Soc. 86 (1914), 2551. — 
7) Berl. Berichte 48 (1915), 117. 
