62 REPORT—1904. 
into which substance the former is easily converted by the action of water. 
When the internal oxide is treated with alcoholic ammonia,' there result 
l-amino-2-hydroxyhexahydrobenzene and two forms of dihydroxycyclo- 
hexylamine, NH(C,H)9-OH)>». 
Power and Tutin ® have isolated a levorotatory modification of quer- 
citol from the leaves of Gymnema sylvestre. It is demonstrated that this 
substance has the same constitution as d-quercitol (pentahydroxyhexa- 
hydrobenzene) which has been established by Kiliani and Schaefer,? and 
can only differ from the latter stereochemically ; but, since d-quercitol has 
(a), + 24°16, whilst the new quercitol has (a);,—73°°9, the one cannot be 
the optical antipode of the other. Eight optically active modifications of 
pentahydroxyhexahydrobenzene are possible, and until a further number 
of these isomerides are known it is impossible to assign a definite con- 
figuration either to d-quercitol or to the new 1-quercitol. 
Aldehydes and Ketones.—The general method for the preparation of 
aldehydes by the action of organomagnesium haloids on the esters of 
orthoformic acid dissolved in dry ether 4 appears to be applicable to the 
syuthesis of hydro-aromatic aldehydes,’ and in this way hexahydro-m- 
toluic aldehyde has been prepared from 3-bromo-1-methylhexahydro- 
benzene. 
The preparation of hexahydrobenzyl alcohol ® has been described by 
Bouveault. Methylhexylearbinol, C,;H,,.CH(CH;)OH, is obtained when 
acetic aldehyde is allowed to act on the magnesium compound of chloro- 
hexahydrobenzene.? When these alcohols are oxidised with chromic acid 
the former yields hexahydrobenzaldehyde and the latter hexahydroaceto- 
phenone. 
Chloro- derivatives of ketomethyldihydrobenzene.*® 
Acids.—When pentane-aye-tricarboxylic acid is digested with acetic 
anhydride and then distilled,® a remarkable decomposition takes place 
with elimination of carbon dioxide and water and formation of 6-ketohexa- 
hydrobenzoic acid. 
CH,—CH,—CO,H CH, 
PO GAG ay eae pCO. CEC. a, 
— CH 
- 00 + CO, + H,0 
CH,—CH, -CO,H : 
\ cH, -- CH, 
On reduction the corresponding hydroxy- acid is obtained, which yields 
trans-6-bromohexahydrobenzoic acid when treated with hydrogen bromide, 
and this bromo- acid, under the influence of sodium carbonate, gives rise 
to A’-tetrahydrobenzoic acid. d-Ketohexahydrobenzoic acid combines with 
hydrogen cyanide to form the mixed nitriles of the cis- and trans-modifi- 
cations of a-hydroxyhexahydroterephthalic acid. Both the corresponding 
acids decompose on distillation with formation of A!-tetrahydroterephthalic 
acid, identical with the acid synthesised by Baeyer.!° 
c-Ketohexahydrobenzoic acid has been used by Perkin !! as the starting- 
point for the synthetical preparation of terpin, inactive terpineol, and 
dipentene ; but as this report does not include a consideration of the 
terpenes and camphors, an account of this work is not given. 
1 Brunel, idid., 1903, 137, 198. 2 J. C. 8., 1904, 85, 624. 
3 Ber., 1896, 29, 1762. * Tschitschibabin, Ber., 1904, 87, 186. 
5 Thid., 850. 5 Compt. Rend., 1903, 187, 60. 
7 Bull. Soc., 1903, 29, 1049. * Zincke, Annalen, 1903, 328, 261. 
8 Perkin, J. C. S., 1904, 85, 416. 19 Annalen, 1888, 245, 160. 
1 
n J. C.S., 1904, 85, 654. 
