- 36 - 



constituent an oxide-like body, carlina oxide, which the author holds 

 to be phenyl- 1 -a-furyl-3 -allene. Semmler 1 ), in conjunction with Ascher 

 is trying to throw further light on this oxide by endeavouring to arrive 

 at a decision between the two isomeric formulae 



HC— CH HC— CH HC— CH 



II II II II II II 



C 6 H 5 .C:C:C— C CH C 6 H 5 .C=C— C— C CH C 6 H 5 .C-C=C.C CH 



H H \/ H 2 \/ H 2 \/ 



OOO 



To attain this object he has tried to effect a synthesis of carlina 

 oxide. Although this synthesis has not been successful, yet in the course 

 of the experiments certain new bodies were discovered, among which 

 we may here mention dihydro carlina oxide. By reducing fural 

 acetophenone (phenyl- i-a-furyl-3-propene- 2 -one- 1) which had previously 

 been obtained by condensing acetophenone and furfurol, the principal 

 product is obtained in the form of the corresponding saturated al- 

 cohol C 13 H 14 2 , which possesses the following properties: b. p. 168 

 to 170 (12 mm.), d^p 1,10, ^d 1,55, mol. refr. found 58,89, calc. for 

 C13 ^-14^2 /~~ 58,97. Analysis confirmed the formula C 13 H 14 2 . From the 

 optical data the authors conclude that the body represents phenyl-i- 

 a-furyl-3-propanol-i, C 6 H 5 . CH(OH) • CH 2 • CH 2 - C 4 H 3 2 ). 



In order to identify this body more closely they prepared from 

 it: the phenyl urethane (m. p. 95,5 to 96 ), the acetic ester (b. p. 171 

 to 1 72° at 11 mm.; d-^- 1,09; n r> 1,526); the ethylic ether (b. p. 145 



20° 



to 147 , d^ 1,055; n n !>545); the chloride, phenyl- 1 -a-furyl-3- 

 chloro- I -propane (b. p. 154 at 10 mm.; d^- I » l 5l n D I >55 2 )- By 

 heating this chloride from 3 to 5 hours in a tube, with an equal weight 

 of melted sodium acetate and twice its weight of glacial acetic acid, 

 to 170 to 180 , hydrochloric acid was given off. The product of 

 reaction possessed the following constants: b. p. 146,5 to 147 (13 mm.), 



ono 



d^ 1,029, n D 1,552. The analysis agreed for C 13 H 12 0. From the 

 above it may be concluded that the splitting-off of hydrochloric acid 

 had resulted in, the formation of dihydro carlina oxide (phenyl - 1- 

 a-furyl-3-propene-i); the equation being as follows: — 



C 6 H 5 • CHC1 • CH 2 • CH 2 • C 4 H s O — HC1 = C 6 H 6 CH : CH ■ CH 2 • C 4 H 3 0. 

 Phenyl- 1 -a-furyl-3 -chloro- 1 -propane Dihydro carlina oxide. 



In its physical constants, dihydro carlina oxide occupied an inter- 

 mediate place between carlina oxide and tetrahydro carlina oxide. 



Cassia Oil. Since our last Report this article has become a 

 little firmer, but on the whole it was possible to maintain the prices 



*) Berl. Berichte 42 (1909), 2355. 



2 ) For details see P. Ascher's Inaug. Dissert., Berlin 1909. 



