Messrs Jones and Kewley, Stereochemistry of Benzene. 123 



considered of some interest to see whether the application of 

 these methods to some benzene derivatives would effect any re- 

 solution. 



The dextro-camphorsulphonate of meta nitraniline was pre- 

 pared by mixing molecular quantities of Reychler's acid and the 

 base. It was found to be a crystalline substance, but was not 

 very suitable for the purpose in hand. 



The dextro-camphorsulphonate of 1. 3. 4 methyl-nitro-amino 

 benzene was prepared by mixing molecular quantities of acid and 

 base in ethyl acetate solution. The salt crystallizes readily in 

 needles of a bright yellow colour which melt to a red liquid at 

 126 — 8° C. The salt is very sparingly soluble in water and its 

 solution in dilute alcohol is of a deep red colour, so that it is 

 unsuitable for polarimetric examination. 



Some 1. 3. 4 methyl-chlor-amino benzene was prepared by the 

 method of Chattaway and Orton (Jour. Chem. Soc. 1900, lxxvii. 

 792) from some of the red oil (3 chlor-para-acetotoluidide) kindly 

 supplied by Dr Chattaway. The salts of this base were found to 

 be suitable in every respect for the purpose in hand. 



1. 3. 4 methyl-chlor-amino benzene dextro-camphorsulphonate 

 was prepared by mixing molecular quantities of the base (101 

 grams) and Reychler's acid (17*9 grams) dissolved in dry ethyl 

 acetate ; on standing in a desiccator the mixture deposited a mass 

 of fine needle crystals which were dried on a porous plate. The 

 salt is colourless, is very soluble in chloroform, but very sparingly 

 soluble in ethyl acetate and acetone. It was repeatedly re- 

 crystallized from a mixture of chloroform and ethyl acetate (1 : 2). 

 Crystallizes as a felted mass of very fine needles which melt at 

 148-5— 149-5° C. 



A specimen on analysis gave the following results : 



I. -2120 grams gave -1222 grams H 2 and -4245 grams C0 2 . 



II. -1990 „ „ -1180 „ H 2 „ -3990 „ C0 2 . 



Found. 



Calculated fox- 



I. II. (C 6 H 3 .CH 3 .C1.NH 2 ) (C 10 H 15 OSO 3 H). 



C. 54-57 547 54-62 



H. 6-40 6-57 642 



Determinations of the rotatory power of the salt in aqueous 

 solutions were made with a triple field polarimeter by Schmidt 

 and Haensch, using sodium light : 



"995 grams in 25 c.c. gave a B = l"07° in a 2dcm. tube, hence 

 [cc] D = 13-44° and [M] D = 50-2°. 



•4130 grams in 25 c.c. gave a fl = -45° in a 2dcm. tube, hence 

 [a] D = 13-62° and [M] B = 509°. 



