55 
second or third methyl alcohol or eth.?r T±nr.e was necessary vhen the filtrate 
from the first was dark colored. In the case of plant a??terial9 inclined 
to resinify on oxidation, the sutstance was extracted \d.th ben?.ene and the 
evaporated benzene extract used for tne oxidation. The disturbing inaterialo 
were insoluble in benzene. 
In 19S5 Tatterjsficld and Martin (l?0) foimd that pure roter.one, vhen 
put through the first portion of the Tekei process, gave a yield of only 
about 80 percent of dehylrorotenone. The renair.der could be recovered from 
the solvents used for the final separation of dehydro compounds. Consequent- 
ly they modified this separation. After dehydration with alcoholic sulfuric 
acidf- the residue wos cooled for some time in ice, the crystals filtered 
by suction and washed successively with a little ice-cold ether, 100 cc. of 
distilled vater, end a few cc. of ice-cold mothyl alcohol. The crys-^.?ils 
wer^ dried at 100° C. and weighed. Tnc filtrate was then separated by add- 
ing 400 cc. of distillod water ard 200 cc. of ether. If a further yield of 
crystals was cbtain'=d, th<>y wer^) filtered, washed with a little ice-ccld 
methyl alcohol, and the weight added to that of the first lot. Tat t^i^rs field 
arid Martin in some cases used the whole ethir extr'-^ct of derris without 
preliminary separation of the rotenone, end in other casta the mother liquor 
from the separation of the carbon tetrachloride co-plex, v?hich they dissolved 
in the alcoholic mother liquor frora the purification of the retenone solvate. 
HightT results were obtained in general by the nicdifii^d method, either 
with or without removal of the rotenone, than by the original '2r'y:ei method 
made on the whole ether extract. 
In the folloving year the same investigators (f4) attempt 3d the 
quantitative preparation of "de-jaelin concentrates" of several samples of 
derris root, following the qualitative scheme used in the earlier i./ork of 
Haller and LalTorge (55). Twenty grams of the roots v/as extracted with 
petroleum ether, with rapid refli?.xin£;, for 55 hours. The evaporated extracts 
were dissolved in ether, and the rotenone was allowed to crystallif.e for 
2 days in the ice chest and then separated. The ether filtrates were then 
extracted vath dilute potash, washed with water, dried cv ;r sodium sulfate, 
concentrated to a s:?:all volume, and placed in the ice chest for 5 days. Any 
further rotenone was separated. Tlie mother liquor fror. this separation was 
termed the "degij.elin concentr.^te'l" It probably contained most of the deguelin 
but may have contained other materials also. The values were somewhat higher 
than those obtained for dehydro compou:ids by the modified Takei method (l20) 
on the alkalii.n soluble portion? of the orif;iaal ether extracts. In t^iis 
work al§o the term "rotenont plus deguelin" was applied to a value calculated 
from the methoxyl content of the alkali-insoluble portion of the extract and 
based on the methoxyl content of rotenone and deguelin of 15.74 percent. 
In using Takci's dehydro meohod 'i^orsley (l3_3) in 1937 found the amount 
of wash solvents rccommcndv^d by Tatt^jrsfi.ad and Martin (l20) to be in- 
adequeto. Accordingly he ador;ted th.- folloving procodur^^i The cooled 
residue from the dehydration process was filtered farough a Gooch crucible 
and Washed with 30 to 40 cc. of ethjr cooled to -10*^ c., the crystals were 
then pressed down and 100 cc. of water coolRd to 2 or 3° C. vfRS poured 
through; . finally methyl alcohol cooled to -10° C. was poured through as 
long as any color was removed. The residue was dried and weighed. In some 
