om. p. 1315 to. 132°. 
ve "On HyeEOBOUeon. this es ae (0) . 
tives ‘not unpleasant smell; b.p. 288 to 289° (Tod as 
solution of. ie with sodium and allyl t Hromiaes ‘oil of a Vi 
b. p. 169 to 172° (740 mm.; d2 0.8960. | Be 
‘Claisen furthermore gives a description of various nitroso and ati 
of mono- and diallylphenols. 2) ENG Se 
3 p-Nitroso-o-allylphenol. (V1), ‘or aylanon monoxime. is ; easily ‘obtained, ‘in form of 
its sodium Salt, by treating allylphenol with the calculated quantities of amyl nitrite 
and concentrated sodium methoxide in’ methylalcohol. The free nitrosophenol melts 
100 to 101°. On reduction of the sodium salt with hydrogen sulphide in ammonia, 
p-aino-o-allylphenol results; m.p. 113.5 to 114°. Heating with acetic auhenae con. 
verts the latter into p-acetamino-o- -allylphenol, m.p, 93°. 3 “Ae 
'  Diallylphenol furnishes, on treatment with amyl nitrite and methylalcoholic. omen 
methoxide, p-nitroso-0,0-diallylphenol or diallylquinone monoxime, m.p. ee to 143°, 
yielding on reduction p-amino-o, o-diallylphenol, m. p. 78.5°. 
The rearrangement of the allyl ether has been investigated by Ciicey ikewise with’ 4 
the aminophenols; the resulting bodies, however, being but of minor interest ey our 
special domain, we omit dealing with them. : é 
Finally, Claisen reports on a synthesis of “eugenol. In an eardier nance) he had 
Stated that in the transposition of guaiacol allyl ether not the ordinary (p-allylguaiacol) 
results, but an isomeride (0-allylguaiacol, o-eugenol). When, however, the ortho position 
in guaiacol is blocked and then the allyl ether prepared, one arrives, after performing 
the transposition, at a derivative of p-eugenol, from which the latter itself i is obtainable 
simply by removing the. blocking group. One starts best from guaiacolcarboxylic 
acid (VII), from which first the methyl! ester (VIII), then the allyl ether methyl ester. (IX) 
is prepared. On subjecting the latter to the rearrangement, the ‘methyl - ester of 
p-allylguaiacolcarboxylic acid (X) results. The free acid (XI) is split up, by boiling 
with dimethylaniline, into CO, and p-eugenol (XII). o-Eugenol is obtained from the 
methyl ester (IX) va the allyl ether of guaiacolcarboxylic acid a which on heating 
yields o-eugenol (XIV). _ 
Methyl guaiacol carboxylate (VII) is obtained best by boiling the acid with methyl 
alcohol and sulphuric acid; m.p. 66 to 66.5°. On boiling this ester, in methyl ethyl 
ketone solution, with allyl bromide, potassium carbonate, and potassium iodide, the 
ether-ester (IX) (2-allyloxy-3-methoxybenzoic acid methyl ester) is formed; b. P: 165. to 
167° (8 mm.). The free acid melts at 65°. When heated in an oil- bath, it. passe fe 
over into o-eugenol (b. p. 250 to 251° at 760 mm.). — i 
The ether-ester (IX), when heated to 230 to 240°, in order to ‘effect he ‘tra S- 
position, is apt suddenly to- begin to boil. very violently, with simultaneous rise 
a 
1 ‘Berl. Berichte 45 (1912), 3161. Liebig’s Annalen » 401 fas 50. oo April si 
