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

  • Salway, Arthur H. (Arthur Henry)
Date:
[1909?]
Catalogue details

Licence: In copyright

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

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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 : ch2< co2h -> CH.< 0] 0 NO 2 and CH0<C CO,H 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 nitroveratric acid: MeOf \cO,H Meo/bNO, , MeO^NcO,H MeOl J, ' -*■ Meol j and MeO' Jno; ' \/ \/ \/ 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 5-nitropyrogallol triethyl ether : e«y doom EtOf Etol J -^ Etol NO, OEt 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< Oi 0 |C02H / OMe ch2< N°2 and CH2<q co2h N0o . OMe OMe * Of the two possible formulae for nitromyristicinic acid, namely NO, •O^NcOnH 1 ^TT ^0 ch2< o'X/ino2 OMe and CH2< 2^0 C02H \/ OMe the former has been adopted throughout this communication, and the same applies in the case of nitromyristicinaldehyde.