3 
NOTES ON SCIENTIFIC RESEARCH. 97 
Homologues of camphor and borneol. 
A few years ago, we discussed a paper by Haller and Bauer’) on dimethylcamphor 
and dimethylborneol and are now in a position to report on the preparation of some 
other derivatives of camphor and of borneol. A. Haller and J. Louvrier*) heated in a 
dry flask 152 g. of dry camphor with 39 g. of sodium amide*) and 500 g. of benzene 
free from thiophene. After the evolution of ammonia had lessened, 155 g. of ethyl 
iodide were added little by little, diluted with an equal quantity of benzene. The 
reaction, which was violent at the beginning, slackened down very soon, so that at 
the end it was necessary to heat for a few hours. In this way 45 to 50 p.c. of the 
theoretically possible quantity of monoethylcamphor were obtained, a body which 
had been prepared before by Brthl*) in a different manner. The reduction of ethyl- 
camphor with sodium and alcohol led to ethylborneol (ethylcamphol). The author 
obtained in a similar way several other alkyl derivatives of camphor and borneol, 
the properties of which are given below in the form of tables: — 
Alkylcamphors and alkylborneols. 
Ben: oe ap Na 
00 
Camphor derivatives 
Monoethylcamphor. . | 108° (14mm.) | 0,927 | -++ 45° Camphorlike smelling liquid. 
Oxime, m. p. 93°. 
Diethylcamphor... . | 132 to 133° | 0,969; -+ 91° Liquid, does not smell any more 
(14 mm.) like camphor. 
Methylethylcamphor . | 112 to 114° | — | + 99°30’ | Liquid. 
(11 mm.) | em 
Propylcamphor®’) ... || 116°(11mm.) | 0,942] + 60°40' | Liquid. Oxime, m. p. 79°. 
Dipropylcamphor... | 157°(14mm.)| — | +53°50’ | Liquid. 
Benzylcamphor®) .. . | = See 40 2 hm, p. O1° 
Dibenzylcamphor.. . | 255°(12mm.)} — | +103°10’ | m. p. 103°. 
Ethylbenzylcamphor . | 193°(11mm.);} — | +91° Viscid. 
Borneo! derivatives | 
Ethylborneol...... 110° (14mm.) | — | +37° Borneollike smelling liquid. Phenyl- 
| urethane, m. p. 47°. 
Diethylborneol .... || 134°(12mm.)| — + 51° Viscid, smells like borneol. Phenyl- 
urethane, m. p. 106° 
Methylethylborneol. . 120° |; — | +38°40" | Viscid. 
(130 mm.)’) 
Propylborneol®).... || 110°(11mm.) | — _ m. p. 59°, 
Dibenzylborneol ... — = = (5S m.p.84°. Phenylurethane, m. p. 82°. 
Cyclocamphanone. By the action of nitrous acid on aminocamphor, a ketone is 
formed, which Angeli*) many years ago called camphenone, as he supposed that 
*) Compt. rend. 148 (1909), 1643; Report October 1909, 199. — 2) Compt. rend. 158 (1914), 754. — 8) Comp. 
Report October 1913, 146. — 4) Berl. Berichte 24 (1891), 3382. — *%) Haller and Minguin had previously 
prepared it. Compt. rend. 142 (1906), 1309; Report October 1906, 134. — %) Haller and March, Compt. rend. 
142 (1906), 315; Report April 1906, 101. — 7) 13 mm.2? — 8) Gazz. chim. ital. 24 (1894), II. 44, 317; Bert. 
Berichte. 27 (1894), 590, 892 (Abstracts). 
7 
