— 130 — 



Acetylcyclohexanone 



y c H 2 — c H 2 

 CH3CO — CH /CH 2 



N C CH 2 



forms a monosemicarbazone of the melting point 159 , and a dioxime. 

 It dissolves readily in alkalies. When the alkaline solution is heated, 

 a complete hydrolytic decomposition occurs, and if hydrochloric acid 

 is added, acetylcaproic acid separates off: — 



CHgCO — CH 2 — CH 2 — CH 2 — CH 2 — CH 2 — COOH. 



This boils at 184 to 185 at 15 mm. pressure, and congeals into a 

 mass melting at 30 . On oxidation with bromine and soda liquor it 

 is converted into normal pimelic acid of the melting point 103 . 

 Acetylcyclohexanone has a mobile hydrogen atom which can be 

 replaced by radicals. Leser for example obtained the ethyl derivative 



, C H 2 — C H 2 v 

 CH 8 CO-C< y>CH 2 , 



I \co CH/ 



which, however, no longer shows the characteristic properties of the 

 /?-diketones. The study of these derivatives is continued. 



Phenols and phenol ethers. 



Behal and Tiffeneau 1 ) have continued their earlier investigations 2 ) 

 of phenol ethers with y-allyl side-chain— C(CH 3 ):CH 2 , and, starting 

 from the three o-, m-, and p-substituted i/;-anethols, y-allyl-p-phenetol, 

 y-safrol, and y-methyleugenol, they have arrived at the following 

 results. On reduction with sodium and alcohol, the y-allyl group is 

 reduced to isopropyl; thus, in the case of isopropylphenetol, the 

 OC 2 H 5 -group was eliminated by hydriodic acid, and the free phenol 

 identified by its melting point and that of its benzoate. If the yj-allyl 

 bodies are oxidised with aqueous chameleon solution in the cold, there 

 are formed, with loss of C0 2 , substituted acetophenones : — 



O 

 R.C(CH 3 ):CH 2 -> R . CO . CH 3 + C0 2 . 



When hypoiodous acid is added, iodohydrins R«C(OH)(CH 3 ) 

 • CH 2 I are formed, which behave differently when hydriodic acid is 

 split off, according to the reagent employed. If they are treated in 



*) Compt. rend. 141 (1905), 596. 

 2 ) Compt. rend. 139 (1905), 139. 



