July 8, 1921] 



SCIENCE 



37 



that ring structures containing a very large num- 

 ber of atoms and connecting the meta and para 

 positions in the benzene nucleus are readily pre- 

 pared. 



The preparation of diliydrohensene and some of 

 its derivatives : E. C. Kendall and A. E. Ostek- 

 BERG. The use of certain sulfonic acids for the 

 dihydration of quinite or of tetrahydrophenol. 

 The yield of dihydrobenzene from quinite by cata- 

 lytic action of phenolsnlfonic acid is practically 

 quantitative. Dihydrobenzene A 1 : 4 adds hydro- 

 chlorous acid and halogens. 



Stability of the C-Sg linTcage in mercury deriva- 

 tives of anisole and plienetole: Edmund B. Middle- 

 ton and P. 0. Whitmoke. The stability of this link- 

 age resembles that of the corresponding linkage 

 in acetylated mercury derivatives of phenol. 

 "While the C-Hg linkage in mercury compounds 

 containing a phenolic hydrosyl is broken quan- 

 titatively by inorganic iodides and similar reagents 

 the C-Hg linkage in the anisole and phenetole 

 compounds is stable to these reagents. The ortho 

 anisyl and phenetyl mercuric halides give the cor- 

 responding E^g compounds. The para com- 

 pounds form the iodides which remain unchanged. 

 Potassium sulfocyanate gives the same results as 

 the iodides with mercurated phenols, their acetyl 

 derivatives, and mercurated anisoles and phene- 

 toles. 



Preparation of mercury ditolyl from tolymer- 

 curio chloride: L. Frances Howe and E. C. 

 Whitmore. Tolylmercuric chloride prepared from 

 toluene sulfinic acid obtained from p-toluene sul- 

 fone chloride was treated with the reagents usu- 

 ally used for changing compounds of the type 

 RHgX to those of the type E»Hg. Metallic 

 copper in alcohol and sodium stannite in water 

 gave very poor yields. Sodium in xylene, aque- 

 ous sodium sulfide, and aqueous sodium thiosulfate 

 gave fair yields. Potassium iodide gave an almost 

 quantitative yield. A new reagent for this pur- 

 pose, potassium sulfocyanate, gave almost as good 

 a yield. Using the sulfone chloride obtained from 

 saccharine manufacture this method is the most 

 convenient for making a mercury diaryl. 



Organic compounds prepared from ortho-chloro- 

 mercuritenzoyl chloride: P. C. Whitmore and 

 Edmund B. Middleton. Preliminary paper. The 

 acid chloride obtained by the action of thionyl 

 chloride on the anhydride of ortho-hydroxymer- 

 curibenzoic acid reacts with alcohols and amino 

 compounds giving mercurated benzoic esters and 

 amides. Compounds have been prepared from 



methyl alcohol, ammonia, aniline, and p-amino- 

 benzoic acid. These compounds are too insoluble 

 for therapeutic use. The action of more complex 

 alcohols and amino compounds is being studied. 



Mercury compounds of normal-hutyl : Euth 

 Walker and P. C. Whitmoke. n-butyl bromide 

 reacts with dilute sodium amalgam giving a poor 

 yield of mercury dibutyl. Mercuric chloride re- 

 acts with butyl magnesium bromide in excess, 

 forming butyl mercuric bromide, calomel, and a 

 small amount of mercury dibutyl. Using an ex- 

 cess of mercuric chloride gives a good yield of 

 butyl mercuric bromide. Heating this substance 

 with an excess of butyl magnesium bromide gives 

 a fair yield of mercury dibutyl, a liquid boiling 

 at 215°. The halide reacts with silver oxide and 

 water giving a water solution of butyl mercuric 

 hydroxide, a strong base. Treatment of this 

 water solution with solutions -of sodium halides 

 gives precipitates of the butyl mercuric halides. 

 The mercury butyl compounds are extremely toxic. 



Mercury derivatives of meta-nitrohensoic acid. 

 Freliminary paper: P. C. Whitmore and V. E. 

 Meharg. Nitrobenzoio acid fused with mercuric 

 acetate gives a mixture of organic mercury com- 

 pounds which are stable to sulfides. One of the 

 compounds is 4-Hydroxymercuri-3-nitrobenzoic 

 acid. The position of the mercury is proved by 

 conversion into 4-bromo-3-nitrobenzoio acid. The 

 mercury compounds are soluble in sodium hydrox- 

 ide and in sodium carbonate. The solution in 

 alkali causes a partial breaking of the C-Hg 

 linkage. The mercury compounds and their reac- 

 tions are being studied further. 



The quantitative determination of paraformalde- 

 hyde: Parrt Borgstrom and W. Grenville 

 HORSCH. Paraformaldehyde was analyzed by four 

 methods and gave by (1) "neutral sulfite" 96.7 

 per cent., (2) iodimetric 96.7 per cent., (3) oxida- 

 tion by dichromate, titration of excess 96.3 per 

 cent., (4) oxidation by permanganate (or dichro- 

 mate) with absorpton of CO, 96.9 per cent, for- 

 maldehyde. Por the ' ' neutral sulfite ' ' use 0.5 N 

 to l.Q N sulfuric or hydrochloric acid, rosolic acid 

 as indicator and 4 N freshly prepared sodium 

 sulfite. In the "iodimetric" method, the base is 

 first added to the paraformaldehyde, then the io- 

 dine solution (0.2 N) within one minute time 

 interval. Increasing this time or changing the 

 order in which the reagents are added lowers the 

 apparent formaldehyde content considerably. The 

 remainder of the analysis is as usual. With other 

 methods, ordinary precautions should be observed. 



