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XXIV.—Supposed condensation of benzil with ethylic alcohol. A correction

 

作者: Francis Robert Japp,  

 

期刊: Journal of the Chemical Society, Transactions  (RSC Available online 1897)
卷期: Volume 71, issue 1  

页码: 297-297

 

ISSN:0368-1645

 

年代: 1897

 

DOI:10.1039/CT8977100297

 

出版商: RSC

 

数据来源: RSC

 

摘要:

JAPP : SUPPOSED CONDENSATION OF BENZIL WITH ALCOHOL. 297 XXIV.-Supposed Conderisation of Bend with Ethylic Alcohol. A Correction. BY FRANCIS ROBERT JAPP, F.R.S. I FIND that the compound described by me, in a paper published jointly with Miss Owens (Trans., 1885, 47, go), as formed by the condensa- tion of b e n d with ethylic alcohol, is in reality identical with Japp and Miller's a.nh~d?.acetonedibe.laxil, C,,H,,O, (m. p. 194-1 95"), and that its formation was due to the presence of acetone in the '' methyl- ated spirit '' (alcohol '' denatured '' with 10 per cent. of crude wood spirit)," which was used instead of duty-paid alcohol in its preparation. We found it necessary to use an enormous excess of spirit in the re- action, and attributed thia to the fact that, with more concentrated solutions, the caustic potash, which we employed as a condensing agent, converts the benzil into benzilic acid; but the true explanation is that this large excess of spirit was required to furnish the requisite amount of the active impurity, acetone.The formula, C30H2404, which we ascribed to the condensation com- pound, requires figures differing only very slightly from those required by anhydraeetonedibenzil. I n the case of the percentages of the various '' solvents of crystallisation "-alcohol, benzene, and acetic acid-which we determined, the differences are smaller still. At the time the paper was published, we believed the compound to be identical with Limpricht and Schwanert's ethy?dibenzo'in, C,,H,,O,, which Jena was supposed to have obtained by the action of alcoholic potash on benzil, the reaction employed by us.On the strength of this belief, we proposed t o alter Limpricht and Schwanert's formula to C30H2404, and we further cast doubt on the existence of an acetyl derivative which these investigator8 had described. I need not say that I greatly regret the publication of these per- fectly baseless criticisms on Limpricht and Schwanert's work. I am indebted to Professor Alexander Smith, of the University of Chicago, for privately informing me that he had not succeeded in pre- paring the compound from benzil and alcohol, and thus calling my attention to the matter. CHEMICAL DEPARTMENT, UNIVERSITY OF ABERDEEN. * For the benefit of foreign abstmctors, the term '' methylated spirit " should always be defined when used ; failing which, I find that they invariably confound this substance with methylic alcohol. Thua in the Juhrmberieht for 1887, p. 954, the abstract of a paper of mine is rendered quite nnintelligible by this blunder.

 

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