156 . REPORT—1905. 
ture be increased to 250°, diphenylamine is completely broken down into 
ammonia and hexahydrobenzene. 
At temperatures of 160° to 180° the methyl and ethyl anilines! are 
readily converted into hexahydro-derivatives without the formation of 
any condensation products, though small quantities are decomposed into 
hexahydrobenzene and a fatty amine. At higher temperatures the re- 
action is much more complicated. 
The preparation and properties of cyclohexyl- mono- and diethylamines, 
and of cyclohexyl- mono- and dimethylamines are described. 
The hydrogenation of m-toluidine, which takes place with difficulty 
at all temperatures, probably because the products are difficultly volatile, 
gives at 200° a mixture of hexahydro-m-toluidine, dimethyleyclohexyl- 
amine and methyleyclohexylaniline. 
Ketones.—1 : 4-diketohexamethylene ? condenses with benzaldehyde 
under the influence of hydrogen chloride to form benzylhydroquinol (3), 
which may be formed by the rearrangement of the benzylidene derivative (1) 
co co C.0H 
O,H,.0H=c / \, CH, jue /\ CH,  0,H,.CH.C ./ SN oH 
1 | C,H,.CH 2 | 3 | 
HC CH, HC CH, no!! | cH 
x vA \Z 
co co C.OH 
or of the norcaran derivative (2). On oxidation with chromic acid it gives 
benzylquinone. Anisaldehyde gives similar derivatives. 
Biltz* has shown that by chlorinating o- and p-hydroxybenzaldehyde 
chlorinated ketotetrahydrobenzenes are obtained. 
1-keto-3-methylhexahydrobenzene gives on treatment with sodamide 4 
a sodium derivative, which reacts with alkyl iodides to give 1-keto-3- 
methyl-6-alkylhexahydrobenzenes. All the ketones described give benzyl- 
idene derivatives, which. on oxidation with potassium permanganate in 
acetone solution give the corresponding a-methyl-a'-alkyladipic acids. 
Alcohols have been prepared from the above ketones by reduction with 
sodium in alcoholic solution. 
3-keto-4-benzyl-1-methylhexahydrobenzene and 3-keto-2 : 4-dibenzyl- 
1-methythexahydrobenzene.® 
Dieckmann and Stein® have been led to the conclusion that the 
formation of C-acetyl derivatives of 1 :3-dicarbonyl compounds by the 
action of acetic anhydride, only takes place under the influence of con- 
densing agents ; ¢.g., dimethyl- and phenyldihydroresorcins with acetic 
anhydride alone give their O-acetyl derivatives (1), which are neutral 
bodies, not giving a colour reaction with ferric chloride, and very readily 
decomposing into acetic acid and substituted dihydroresorcin. 
C(CH;). C(CH,)» 
H.C / CH, HO, / SeGE. 
ee Be 
CH,CO.00 co ale CO 
: YS MS 
CH CH.CO.CH, 
Sabatier and Senderens, Compt. Rend., 1904, 188, 1257. 
Stollé and Moering, Ber., 1904, 37, 3486. 
Ber., 1904, 37, 4003. 4 Haller, Compt. Rend., 1905, 140, 127. 
Haller, Compt. Rend., 1905, 140, 624. 5 Ber., 1904, 87, 3370. 
0 bb = 
