Wallach?) abeined:: many years ago, on te menthone with benzaldenyee 
_ in the presence of hydrochloric acid, a benzylidenementhone hydrochloride, to which 
Eatin’ assigned the formula I. E. Boedtker®) tried to determine the constitution of 
_ this body by adding 5 g. of aluminium chloride to a solution of 25 g. of benzylidene- 
Pe eehtione hydrochloride in 500 g. of benzene. After some days, when the evolution 
P of hydrogen chloride had ceased, the mixture was poured into water, then dried and 
a the benzene distilled off. As chief product, a body melting at 159° was obtained, 
which proved to be identical with a diphenylmenthylmethane, obtained by Boedtker 
2 through the action of magnesium phenyl bromide on benzylidenementhone‘). As by- 
ze: products, benzylidenementhone and a stereoisomeric diphenylmenthylmethane (m. p. 135 
a Z - group, Wallach and Martine’s benzylidenementhone hydrochloride must have the struc- 
= ture of a menthophenylchloromethane, as expressed by formula Il. 
‘x 
yy 
* ‘On condensing menthone with benzaldehyde in the pres:nce of hydrochloric acid, 
_ Martine had obtained as by-product a chlorinated oil, which Boedtker investigated — 
3 “more closely and recognized to be a mixture of stereoisomeric menthophenylchloro- 
_ methanes. It was impossible to induce it to crystallize. By heating with alcoholic 
potash lye under a reflux condenser, the mixture is converted into a new isomeric 
__benzylidenementhone (a-benzylidenementhone). It is a yellow oil, boiling at 189° 
principal products benzoic acid, «a ‘-methylisopropyladipic acid and «-isopropylglutaric 
_ acid. When boiled with concentrated alcoholic potash lye, it forms menthone, benzoic 
acid and benzyl alcohol. The reaction with magnesium phenyl bromide leads to an 
= isomeric diphenylmenthylmethane (m. Pp. 156 to ee 
1B | Cl 
Zee ; CCICH2C.Hs ere: CHCH 
f ; as Fis < Cs His< | | a CoHs 
Pe ni eR) CO 7 
fie. ~ (1) Benzylidenementhone hydrochloride (II) Menthophenylchloromethane. 
according to Martine. 
_ Camphor. On page 63 of our October Report 1915, we discussed a publication by 
__ H. Rupe®) concerning the influence of constitution on the rotatory power of optically 
active substances. Experimental details regarding the preparation of derivatives. of 
a eee camphor have now been described elsewhere by Rupe together with M. Iselin®). — 
4 Owing to the presence of the conjugation of the ethylenic and ketonic linkings in 4 
C:CH-R_ 
& the derivatives of methylenecamphor of the type CsHuc - Co , these substances 
Si __ supply attractive material for such investigations. 
, « (Thése, Paris 1904, page 66). — *) Bull. Soc. chim. IV. 17 (1915), 374. — *) Compt. rend. 145 (1907), 329; 
Report October 1907, 160. — 5) Liehigs Annalen 409 (1915), 327. — %) Berl. Berichte 49 (1916), 25. 
4) Liehigs Annalen 305 (1899), 261; Report October 1899, 64. — 2) Contribution & 1’étude des menthones = 
_~to 136°) had formed. As in Friedel-Craft’s reaction chlorine is replaced by the phenyl ae 
— (12 mm.). On being oxidized with potassium permanganate in acetone, it yields as ~ ee 
% 
bogs 
a ae ot ey t 
SRA Nair) Stupaediy Ah aera 
RWC EL a ona teen Og Ng aah 
