478 Mr Mills, Mr Parker and Mr Prowse, On the Resolution, a 
On the Resolution of 5-Nitrohydrindene-2-carboxylic Acid. 
W. H. Mitts, M.A., Jesus College, H. V. Parker, B.A., and R. 
Prowsg, B.A. 
[Read 18 May 1914.] 
With the object of obtaining an optically active derivative of | 
benzene in which to account for the optical activity it would be | 
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By | 
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t 
necessary to take into consideration the relative distribution in | 
space of the groups attached to the benzene nucleus 5-nitrohy- 
drindene-2-carboxylic acid (III) has been prepared and has been | 
shown to be resolvable into two optically active components. 
The racemic compound was prepared by nitrating hydrindene- | 
2-2-dicarboxylic acid (I) and eliminating one carboxyl group from 
the product by heating in an indifferent solvent. 
OH, 
if Cir ye (CO,H),, 
CH, 
it NO,0,H ree _ 8 (CO,H)., 
ieee aes NO,C,H i eee H. 
CH, 
D} 
4 
The position of the nitro group was established by oxidising | 
the nitrodicarboxylic acid (II) with potassium permanganate, | 
The product was 4-nitrophthalic acid from which it follows that 
in nitrohydrindene carboxylic acid the nitro group must occupy | 
the 5-position. 
at. oe 
Seg" 
ae CO,H. 
The acid was resolved by means of quinine, the recrystallised — 
quinine salt giving on decomposition the /-acid. The d-acid after — 
extraction from the quinine salt mother liquors was separated — 
from the accompanying racemic acid by crystallisation from 
benzene in which the latter is relatively sparingly soluble. The 
racemic acid melts at 122°, the active acids at 116°. The specific 
rotation of the active acids for the mercury green light is 
flellecn a 36°4 and — 36°5°. 
