October 27, 1922] 



SCIENCE 



491 



that fractional distillation, selective sulfonation, 

 crystallization of the sulfonic acids and selective 

 hydrolysis of the xylene sulfonic acids all tend 

 to bring about a partial separation of the three 

 xylenes present in coal tar xylene, but that none 

 of these processes alone is entirely suitable for 

 the isolation of the ortho and para derivatives. 

 A satisfactory procedure is described in which the 

 above processes are combined. 



The preparation of tetrametliylene 'bromide: 

 C. S. Makvel and A. L. Tanenbaum. Tetra- 

 ruethylene bromide is a research chemical often 

 needed. Several methods have been devised for 

 its synthesis, but none of these is satisfactory. 

 It has been found possible to obtain the sub- 

 stance easily by the following reactions: 

 Br(CH2)3Br"+ CeHgONa — Ph-0(CH2)3Br, + 

 NaCN + EtOH + H2SO4 — Ph-O(0H2')3CO2Et, 

 + Na + EtOH — Ph-0(0H2)3CH20H, + HBr 

 — Ph-0(0H2)3CH2Br + Br(CH2)4Br. The 

 yields in the steps are 80, 90, 80, 65, 40 and 40 

 per cent, respectively. As will be noticed the 

 yields are good in every step except the last, 

 where equal amounts of phenoxybutyl bromide 

 and tetrametliylene bromide are obtained. The 

 former can be converted into the latter by pro- 

 longed treatment with hydrobromic acid. Hydri- 

 odic acid reacts like hydrobromic acid, giving 

 about the same yields of the iodine compounds. 



Some derivatives of ethylbenzene: F. W. Sul- 

 livan, Jr. Ethylbenzene was prepared in good 

 yield by the action of ethj'lene on benzene in the 

 presence of aluminum trichloride. It was found 

 that chlorine acts on boiling ethylbenzene giving 

 alpha ohloroethj'l benzene and not the beta com- 

 pound as is stated in the literature. The cor- 

 responding bromide was prepared. Both give 

 phenyl methyl carbinol on hydrolysis. They also 

 give an acetate when boiled with sodium acetate 

 in glacial acetic acid. Styrene is obtained by 

 passing the vapors of chloroethyl benzene over 

 soda lime. The same substance is obtained in 

 quantitative yield when the chloro compound is 

 heated with quinoline. Ethyl benzene gives very 

 good yields of the nitro derivatives when nitrated 

 according -to the standard procedure for the 

 nitration of toluene. 



The preparation of aromatic alpha hydroxy 

 acids and their esters from the cyanhydrins : 

 G. E. Seil and Is. Kaltjgai. Sell's method of 

 hydrolysis of the cyanhydrins by means of sul- 

 furic acid dihydrate was used on mandelic nitrile 

 prepared from benzaldehyde. The yield of man- 

 delic acid was 83 per cent. The ethyl ester was 

 prepared by different methods. The isopropyl 



ester of mandelic acid was syntliesized and its 

 properties were determined. 



The preparation of methyl red: A. W. ScHOR- 

 GEB. Methyl red is prepared by diazotizing an- 

 thrauilic acid and coupling with dimethylaniline, 

 following in general the procedure of Tizard and 

 Winmill. Free methyl red in the form of violet 

 crystals is best obtained by crystallization from 

 acetic acid, the crystals retaining two molecules 

 of the solvent. Prom the standpoint of ease of 

 crystallization and purity of product, the best 

 procedure is to crystallize from dilute hydro- 

 chloric acid, obtaining the hj'drochloride of 

 methyl red. The sodium salt has also been pre- 

 pared and like the analogous compound, methyl 

 orange, is readily soluble in water. 



Neiu heterocyclic arsenic compounds: C. S. 

 Palmer. In the presense of two moles of sodium 

 ethylate, one mole of primary arsine condenses 

 with one mole of beta-beta-dichlorodiethyl ether 

 or gamma-gamma-diehlorodipropyl ether to give 

 compounds such as 



CHo— CH2 



Ar — As 



O 



CH2— OH2 

 The products are high-boiling, stable oils. They 

 give the reactions of tertiary arsines, the arsenic 

 readily passing to the pentavalent state by the 

 addition of oxygen, sulfur, halogens, alkyl halides. 

 Chloroplatiuates and mercuriehlorides are also 

 formed. The above synthesis is a new reaction 

 of primary arsines. Preliminary experiments 

 show that the method can be applied to secondary 

 arsines and to other halides as well as to dihalo- 

 genoethers. 



Action of arsenious chloride on quinoline: 

 John H. Schmidt. (By title). Carbostyril and 

 a product which preliminary analyses indicate to 

 be tricarbostyril arsonio acid have been prepared 

 by the action of arsenious chloride upon quinoline 

 at comparatively high temperatures. Further 

 investigation of this reaction is in progress. 



On the basis for the physiological activity of 

 certain onium compounds. II. Arsenic deriva- 

 tives: E. E. Eenshaw and E. E. Wagner. Sev- 

 eral new arsonium compounds are described. Tri- 

 methyl arsine dihalides condensed with ethylene 

 and with formaldehyde to form the arsenic analog 

 of neurine and formaldehydo trimethyl arsonium 

 halides respectively. 



The behavior of the mercuric salts of car- 

 boxylio acids toward heat and the structure of 

 mercuric cyanide: Morris S. Kharasch and 



