ah 
A . and A) differ pe nt aa he same as the b. ps. (143 to 1440 at 10 mm. 
| anding does not show any inclination to crystallize. In their opinion, the solid 
eahtchyde prepared by Semmler and Bartelt must be a polymeride, the more so as 
ethyl acetate and 75 cc. of ether. 
Chavicol methyl ether can, by way of the ozonide, easily be converted into. homo- 
: _anisaldehyde, a colourless, highly refractive oil, b. p. 78 to 79° (1.4 to 1.5 mm.), which 
____ in dilution smells like heliotropin. d*° 1.096; np» 1.53593. The semicarbazone melts 
on Phetwecn 175 and 176°, the pnenea arene at 95°. 
; It was in no way possible to obtain the corresponding aldehyde of myristicin. by 
~ reduction e the ozonide. Apiole behaved in a similar way. 
ay 
The phenols of Japanese lac. In a series of treatises by R. Majima, J. Nakamura _ 
and J. Kurosawa‘) on the chief component of Japanese lac, we find described some — 
reactions, the knowledge of which is interesting also for our special domain. In order 
Eto synthetize the isohydrourushiol dimethylether’), Majima and Nakamura condensed — 
a methylvanillin with methyldodecyl ketone, dissolved in absolute alcohol, by adding a 
solution of sodium hydroxide. Crystals separated gradually and after a fortnight the ee 
po reaction was completed under formation of a substance, 
* : 4. (CH;0),’°CgHs-CH: CH: CO-(CH2)11CHs, 
‘. m. p. 67 to 68°. On being reduced in ethereal solution with platinum black and 
hydrogen, the substance took up two atoms of hydrogen, forming the saturated ketone 
(CH; 0), CeHs- (CH2)2-CO-(CHs)11-CHs, m. p. 61 to 62.5°. After having been heated for 
ten hours on a sand-bath with 15 times its weight of amalgamated zinc and hydro- 
chloric acid, this saturated ketone was reduced to iéschydrourushiol dimethylether, 
om, p. 50 to 51°. It was identical with the compound obtained by condensation of 
_ was heated with hydrobromic acid, when isohydrourushiol resulted, m. p. 91°. 
In a similar way, 3 peop meson, ea carey Nenzele was prepared from methyl- 
vanillin and methylundecyl ketone. 
1-n-propyl-2, 3- -dihydroxybenzene, prepared by Kurosawa from o-eugenol, resembles | 
_ the hydrourushiol in structure. Kurosawa reduced o-etigenol*) with platinum black 
and hydrogen to o-dihydroeugenol, which he demethylated by means of hydrobromic 
acid, when the 1-n-propyl-2,3-dihydroxybenzene formed, m. p. 70 to 72°. Through 
heating o-eugenol with sodium ethylate and dimethyl sulphate in alcoholic solution, 
Bi _ Kurosawa obtained o-eugenol methyl ether, which he reduced with hydrogen and 
~ platinum black into 1-n-propyl-2,3-dimethoxybenzene. In a like manner, _1-n-propyl-— 
‘ 3,4-dihydroxybenzene and 1-n-propyl-3, 4-dimethoxybenzene aiiyerome nyleieeaen were 
\ prepared from eugenol. | 
structure has not been established completely so far. Hydrourushiol has been recognized by Majima (Beri. 
aed Berichte 48 [1915], 1593) to be 1-n-pentadecyl-2, 3-dihydroxybenzene. Jsohydrourushiol distinguishes itself from 
*) See Report April 1914, 144, 
: gr 
295 according to S., 42° 1.2626 o 
r to rS.; 137° at 10 mm. according to H. and A.). The aldehyde obtained by 
. and Adam is a very liquid, almost colourless oil, which even after long 
ae itself melts already at 37°. In order to prepare the homopiperonal, the 
_ Safrole ozonide, which is insoluble in ether, was reduced in a mixture of 75 cc. of © 
veratrol with n-pentadecylic acid in the presence of aluminium chloride and by conse- 
cutive reduction. In order to prepare the isohydrourushiol from the dimethylether it 
*) Berl. Berichte 48 (1915), 1597, 1603. — 7) Urushiol is the chief component of Japanese lac. Its 
é _~ hydrourushiol by the position of the pentadecyl group. It is a 1-n-pentadecyl-3,4-dihydroxybenzene. — e ; 
