The action of nitric acid on the ethers of aromatic hydroxyaldehydes / by Arthur H. Salway.

  • Salway, Arthur Henry.
Date:
1909
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Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The action of nitric acid on the ethers of aromatic hydroxyaldehydes / by Arthur H. Salway. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    myristicinaldehyde takes place to the extent of 60‘6 per cent. Piperonal, on the other hand, yields only 30 per cent, of 4-nitro-l : 2- methylenedioxybenzene, whilst with anisaldehyde substitution of the aldehydic group does not occur. Although the direct displacement of the aldehydic group of the ethers of aromatic hydroxyaldehydes by the nitro-group has not hitherto been observed, an analogous transformation, in which the carboxyl group of the corresponding ethers of aromatic hydroxy-acids is eliminated with simultaneous nitration, has long been on record. Thus Jobst and Hesse {Annalen, 1879, 199, 70) have shown that when piperonylic acid is acted on by concentrated nitric acid, it is converted into a mixture of 4-nitro-l : 2-methylenedioxybenzene and nitropiperonylic acid : CH,< CO^H CH,< NO 2 and CH,< COoH no; A similar reaction has been observed by Tiemann {Ber., 187G, 9, 936) in the case of veratric acid, which yields on nitration 4-nitro- veratrole and niti’overatric acid: MeOf MeOl fCOgH MeOf^NOo MeOl MeO /\ COgH MeOl jNO '2 and ■\/ —X/ Furthermore, Weselsky and Benedikt (Ber., 1892, 25, 722) have shown that the triethyl ether of gallic acid is almost quantitatively converted by nitric acid into 6-nitropyrogallol triethyl ether: Eto/\ Eto!^ OEt ^OOgH EtO EtO NO. \/ OEt In addition to these observations, the present author has investigated the action of nitric acid on myristicinic acid, and has found that a similar reaction ensues with the formation of a mixture of 5-nitro-l- methoxy-2 : 3-methylenedioxybenzene and nitromyristicinic acid :* CH2<° C02H \/ OMe CH„< /\ NO \/ OMe 2 and CH.< Of^COgH OI^^NO^ . OMe Of the two possible formulas for nitromyristicinic acid, namely : NOj CH2<oI^^NO^ and OMe OMe the former has been adopted throughout this communication, and the same ajqilies in the case of nitromyristicinaldeliyde.
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