76 REPORT OF SCHIMMEL & Co. OCTOBER 1915. 
ethoxide, it leads to components which boil very much higher. The sodium ethoxide of 
acts first condensing on two molecules of cyclopentanone, whilst the hydrogen evolved 
further reduces the ketone formed to the saturated alcohol. The cyclopentanone was 
prepared by distilling adipic acid with barium hydroxide. The reduction with the aid 
-of sodium, ordinary ether and water only yields 33.4 p.c. of cyclopentanol. From the 
high-boiling products of the reaction, «-cyclopentylcyclopentanol and the pinakone 
CioHigO2 (m. p. 108°) were isolated. If the former is oxidized with chromic acid it 
forms «-cyclopentylcyclopentanone, which with benzaldehyde yields a condensation 
product, Ciz7H2.O, melting at from 97 to 98°. According to Wallach’s directions’), 
a-cyclopentyleyclopentanol was converted into «-cyclopentylcyclopentene, which affords 
a rather unstable ozonide. 
Hydroaromatic compounds with gem-dialkyl groups. 
Some time ago already, K. von Auwers and E. Lange’), in a paper on hydro- 
aromatic alcohols and ketones with a gem-dimethyl group, described some bodies 
related to the terpenes, e.g. 1,1-dimethylcyclohexanol-4, 1,1-dimethylcyclohexanone-4, 
1,1,4-trimethylcyclohexanol-4, 1,1-dimethylcyclohexanol-2, 1,1-dimethylcyciohexanone-2, 
1,1,2-trimethylcyclohexanol-2, 1,1-dimethylcyclohexanol-3 and 1,1-dimethylcyclohexanone-3. 
The same authors*) now publish a second paper on these compounds, reporting 
on some hydrocarbons, alcohols and ketones with several gem-dialkyl groups. The 
properties of the bodies described in this and in the previous publication are given 
below in tabulated form. 
Of the ten possible isomeric trimethyleyclohexenes with a gem-dimethyl group, 
the authors have so far prepared the 1,1,4-trimethylcyclohexene-3 and the 1,1,2-tri- 
methylcyclohexene-2. On oxidation of the former an oily ketonic acid, CoHi.QOs, 
results as chief product and, besides, an unsaturated ketone, CyHisO. This acid may 
perhaps -be the $-dimethyl-0-acetylvaleric acid, a compound allied to the geronic 
and isegeronic acids. 
Experiments of preparing saturated and unsaturated hydrocarbons from tetra- 
alkylated cyclohexanols always yielded mixtures of inconstant boiling point and from 
which it was impossible to isolate uniform compounds. 
Many of these bodies have previously been described by others, but the constants 
given below are only those observed by Auwers and Lange. 
b. p. d2- Np m. p. 
1,1-dimethyleyclohexanone-4 . . . . 72 to 73.4° (14 mm.) 0.932 1.45374 (24.29) 38 to 40° 
1,1,4-trimethylcyclohexanol-4 . . . . 75° (11 mm.) a — 58° 
1,1-dimethyleyclohexanol-2.. ... . 77 to 78° (14 mm.) 0.929 1.46521 (24.1°) — 
1,1-dimethyleyclohexanone-2 . . . . 172 to 172.5° (757 mm.) 0.915 1.44903 (20.49) — 
1,1, 2-trimethylcyclohexanol-2 . . . . 75.89 (16 mm.) 0.926 1.46866 (18.4°) 
1,1-dimethylcyclohexanol-3. . . . . 73 to 74° (8 mm.) 0.909 1.46149 (13.79) 
1,1-dimethylcyclohexanone-3 . . . . 54° (8 mm.) 0.906 1.44763 (18.69) - 
1,1-dimethylceyclohexanol-4.. . . . 76.5° (9.5 mm.) + 0.925 1.4639 (20°) 
1,1-dimethyleyclohexene-3 . . . .. 120 to 122° (750 mm.) 0.804 1.4456 (20°) 
119.5 to 121.2° (767 mm.) 0.803 1.44521 (20°) 
1,1,4-trimethyleyclohexene-3 . . . . 140° (ordinary pressure) 0.802 to 0.805 1.4454 to 1.4469 (20°) 
1,1,2-trimethylcyclohexene-2. . . . . 146.2 to 147.29 (767 mm.) 0.822 to 0.826 1.4562 to 1.4566 (20°) 
1,1,4,4-tetramethylcyclohexanol-2 . . 201.5 to 203° (745 mm.) 0.901 1.4618 (20°) 
1,1,4,4-tetramethylcyclohexanone-2. . 190.4° (758 mm.) 0.888 1.4459 (20°) 
1,1- dimethyl-4, 4-diethylcyclohexanol-2 . 117 to 118° (11 mm.) 0.915 1.4730 (20°) 
1,1- dimethyl-4, 4-diethyleyclohexanone-2 233 to 235° (742 mm.) 0.907 1.4609 (20°) 
1) Liebigs Annalen 230 (1885), 257. — 2%) Ibidem 401 (1913), 303. — *%) Ibidem 409 (1915), 149. 
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