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NOTES ON SCIENTIFIC RESEARCH. | 139 
; -When_hydroxymethylene camphor is hydrogenated, several by-products are formed, 
: inter alia. methylene camphor {V), a very volatile substance with a strong, camphoraceous 
smell. On treatment with hydrobromic acid in glacial acetic acid solution, camphyl — 
-bromomethane (Ill) results. With bromine in chloroform solution, methylene camphor 
yields the dibromide, m.p. 108 to 109°. : 
3 On abstracting hydrogen bromine from camphyl bromomethane by means of methyl- 
_ alcoholic potash, or better on heating camphyl carbinol with alcoholic potash, chemically 
_ pure methylene camphor is obtained; m.p. 43.5 to 44°; b.p. 85 to 85.5° (9 mm.). The 
preparation obtained by Minguin‘) on boiling bromomethy! Sty aie with alcoholic 
_ potash (m.p. 30 to 35°) was but impure. 
From methylene camphor, there’ resulted, on Pearaeenation: as by-product methyl 
camphor (V1) which may be separated from methylene camphor by converting the latter 
into its hydrobromide and extracting the methyl camphor from the filtrate of the hydro- 
_ bromide with ether. It is obtained in the purest state by reducing methylene camphor; 
_ m.p. 37.5 to 38.5°; b.p. 88 to 89° (8.5 mm.). 
C:CH-OH CH: CH, OH 
. Cs eee [i =A + H,..= CsHus< | 
BL Se 
4 (1) Hydroxymethylene camphor. (II) ane carbinol. 
4 SH: -CHSBr aca CH,:-O-CHO 
3 oe C ios . 
- (111) Camphyl ee (I1V) Formyl a os of camphyl carbinol. 
1 C : CH: : CH ; CH; 
: CoH | - CoH | 
4 , Ge" ! : ee) 
E (V) Methylene camphor. (VI) Methyl camphor. 
4 The authors explain the formation of methylene camphor as a by-product by means 
of the dehydrating action of the nickel poms on a small part of the camphyl carbinol 
formed. 
A by-product fraction, b.p. 88 to 110° (10.5 mm.) yielded, on treatment with methyl 
alcoholic potash, methylene camphor and methyl camphor. The authors are of opinion 
that in this case methylene camphor is formed by splitting up of the ethyl ether of 
camphyl! carbinol which in turn resulted from the addition of ethyl alcohol to gan 
camphor. 
Another by-product fraction, b.p. 110 to 138° (10.5 mm.), yielded on boiling with 
alcoholic potash methylene camphor and hydroxymethylene camphor, and the authors 
suspect, therefore, amongst the by*products also the ethyl ether of hydroxymethylene 
camphor, whose formation is due to a condensation, under the influence of nickel, of 
hydroxymethylene camphor and ethyl alcohol. 
ae me 
nL a SEI a Rael 
? 
/ 
A. Tschirch”) gives a retrospective review on the present knowledge concerning 
_resinols and resinotannols. Towards the end of his noteworthy publication the author 
: advances the opinion that the resinotannols are not protoretines, but teleutoretines and 
correspond to the final bases, saponines, and other products resulting from primarily- 
formed bodies. From the view of the evolution doctrine, the resinotannols follow the 
ae POISE 
*) Compt. rend. 136 (1903), 752. — *) Schweiz. Apoth. Zty. 57 (1919), Nes 5 and 6. 
