PACH, Me Rea thee PLOT PTE Se 5, SD 
% sue ey Jon: Sup 
; 4 yu. * f 
4144 
‘the latter. Yiowes it is to be assumed ‘that vanttieaa’ is an c-glucosic 
synthetically obtained ester belongs to the 8-glucosides. 
OCs? OCHO CH: : 
CsH ASI CoHac CeHs<-OCeH1105 
COOH t. COOCH. 7 Seams 
(1) B-d-Glucoside-ocesalicylic (i) Gaultherin. (III) @-d-Glucoside-o-2-hydroxy- 
acid. 4~methoxybenzoic acid. 
They were further successful in preparing the §-glucoside of 2hydroxy-eeee axY- 
benzoic acid (m. p. 163°) (II). The methyl ester of this compound is only distinguished b; 9) 
the sugar radicle from the primverin (IV)*), occurring in the roots of many Primula species. a 
The synthesis of the methyl ester of 6-tetracetyl-glucoside-o-anthranilic acid (m. p. a : 
: -was also accomplished. The corresponding natural glucoside has hitherto not been found, 
Bee ‘but probably occurs in nature, since the methyl ester oe anthranilic acid is contained i in 
‘many volatile oils. 
' . ! Nitrogenous Bodies. 
The action of cyanogen bromide on hydrocarbons and phenol ethers in the presence 
.of aluminium chloride has been studied by P. Karrer, A. Rebmann, and E. Zeller?). 
In general the nitrile was easily formed, as.in the case of acenaphthene (I) and thio- - 
phene (II). m-tertiary butyl-toluene and naphthalene gave worse yields; acenaphthylene, 
indene and diphenyl formed no nitrile with cyanogen bromide and aluminium chloride. 
Cyanogen chloride can be used in place of cyanogen bromide for the synthesis; 
cyanogen iodide is to be less recommended, since much iodine is split off when using it. 
If old, and hence probably polymerized, cyanogen bromide is used, instead of fresh, no 
monomeric nitrile is obtained, but polymeric compounds. Benzene, for example, when © 
treated with old cyanogen bromide yielded the trimeric kyaphenine (III), but not benzonitrile. ~ 
From phenol ethers, which gave still better results than the hydrocarbons, the 
cyanides of the following compounds were prepared:—of phenetol, «-naphthol-ethyl — 
ether, neroline, veratrole, pyrogallol trimethyl ether, resorcinol dimethyl ether ihysoa 
CH CH 
Hee Sc_cr, CHE CCN Noe Cols 
| S—€. | one 
pre ae C—CH, CH CH : é. CoH. 
CH CH (Il) a-Thiophene cyanide (IH) ne 
(1) Acenaphthene ,cyanide (a-thiophenecarboxylic acid nitrile). 
dimethyl ether. On saponifying 1-cyano- -2-methoxy-naphthalene with caustic ota he 
solution the related carboxylic acid was not obtained, but solely its amide. The reason _ 
probably is, that the CN-group is sterically hindered through the occupation of the two ortho- 
positions. The CN-group was always found in the ortho- or para-position to other groups. 
Along with the phenol-ether cyanides small quantities of hydroxy nitriles were | 
also formed: from the phenol-ether cyanides during the reaction, by the boo 
effect of the water-free aluminium chloride. 
ae es Ee i a ee es 
1) Cf. Report April 1913, 85. — 2) Helvet:Chim. Acta 8 (1920), 261; cf. ibidem 2 (1919), 89; Report 1919, 146. % 
SIZ, 
7i~N 
