

22 Report of Schimmel § Co. April /October 1917. 



potash and sulphuric acid apparently transformed the terpene alcohols into a mixture 

 of citral and citronellal. Even prolonged boiling over sodium did not make the fractions 

 boiling between 125 and 135° (12 mm.) free from oxygen owing to the presence of a 

 sesquiterpene ketone Ci 5 H 2 6 0. They contained a hydrogenated monocyclic sesqui- 

 terpene Ci 5 H 2 6, ferulene. ■ In order to remove the ketone, Roenisch reduced the fractions 

 with sodium and alcohol, whereby the ketone turned into the alcohol Ci 5 H 2 8 which 

 he then destroyed by boiling with sodium. The purified hydrocarbon thus obtained 

 gave the following constants: boiling point 126 to 128° (10 mm.); d 20 o 0.8687; « D + 6°; 

 n D20 o 1.48377. Ferulene was also freed from the ketone by other means, namely, by 

 treatment with hydroxylamine. The ferulene thus produced . gave the following con- 

 stants: boiling point 124 to 126° (7 mm.); d 20O 0.8698; a D -f 6°; n D20O 1.48423. These lead 

 to the conclusion that it is not quite pure. It contained two double bonds which could 

 be hydrogenated by means of platinum and hydrogen, thereby forming tetrahydroferulene 

 which boiled between 118 and 122° (10 mm.) and gave the following constants: d 20O 0.8400; 

 « D -j-4.2°; n D20O 1.45810. 



The aliphatic ketone Ci 5 H 26 0, doremone, also occurs in the fraction boiling between 

 140 and 155° (10 mm.); after purification by means of repeated distillation it gave the 

 following constants: boiling point 145 to 155° (12 mm.); d 20 o 0.8765; « D -f- 3° 30'; 

 n D20O 1.47160. The oxime melts at 88°, the semicarbazone at 124°. The ketone could 

 not be recovered from the oxime. Sodium and alcohol as reducing agents transformed 

 the doremone into doremol which boiled between 145 and 150° (12 mm.) and gave the 

 following constants: d 20 o 0.8702; « D + 3°; n D20 o 1.47130. On hydrogenation by means 

 of platinum and hydrogen; this produced the saturated alcohol, Ci 5 H 32 0, tetrahydro- 

 doremol, boiling between 140 to 145° (12 mm.), and showing the following constants: 

 d 20O 0.8403; « D + 2°48'; n D20O 1.44817. When reduced by means of platinum and hydrogen 

 doremone is transformed into tetrahydrodoremone which boils hetween 142 and 144° 

 (12 mm.) and gives the following constants: d 20 o 0.8434; « D +1°24'; n D20O 1.44803. 

 Doremone is the first aliphatic sesquiterpene ketone found in a natural state. 



On being treated with acetic anhydride and sodium acetate, doremoneoxime is 

 transformed into an acetate, which leads to the conclusion that a ketoxime is present, 

 as aldoximes produce nitriles under these circumstances. 



Roenisch obtained by means of repeated fractional distillation of the higher- 

 boiling compounds of ammoniacum oil an acetate of an aliphatic sesquiterpene 

 alcohol, doremylacetate, which showed the following constants: boiling point: 155 to 

 165° (12 mm.); d 20O 0.8896; « D -f-4°48'; n D20O 1 .46596. The free alcohol, doremol, boiled 

 between 145 and 155° (12 mm.); d 20 o 0.8723; « D + 3 ° 30 " ; n D20 o 1.47216. It appears to 

 be identical with the doremol obtained by reducing doremone, as platinum and hydrogen 

 first produced dihydrodoremol boiling between 140 and 150° (12 mm.) and giving the 

 following constants: d^o 0.8584; a D + 3°; n D20 o 1.45916, this being subsequently trans- 

 formed into tetrahydrodoremol. 



The fraction of the gum ammoniac oil boiling above 175° (12 mm.) became, on 

 cooling, a solid mass resembling paraffin, which contained a paraffin alcohol, Ci 6 H 3 4 0, 

 melting at 48°, the latter being highly probably identical with cetyl alcohol. Hitherto 

 this had only been found in the animal organism. 



Hyssop Oil. We were in a position to distil fairly large quantities of hyssop of 

 our own growing and shall be able to extend our fields still further after the war. 

 We may hope then to succeed in eliminating little by little all imports of French oil, 

 which, by the way, does not come up to ours. 



