Mercuration of nitrohydroxybenzaldehydes / by T.A. Henry and T.M. Sharp.

  • Thomas Anderson Henry
Date:
[1924.]
Catalogue details

Licence: Public Domain Mark

Credit: Mercuration of nitrohydroxybenzaldehydes / by T.A. Henry and T.M. Sharp. Source: Wellcome Collection.

    3/16
    CXXT.—Mercurcition of Nitrohydroxybenzaldehydes. By Thomas Anderson Henry and Thomas Marvel Sharp. In a previous paper (J., 1922, 121, 1055) mercury compounds* derived from the three hydroxybenzaldehvdes were described and their constitution established * except as regards the acetoxy- mercuri-ra-hydroxybenzaldehyde. It is now shown that the- mercury in this substance must be in position 2, with respect to the aldehyde group, since on its replacement by the nitro-group there- is formed the known 2-nitro-3-hydroxybenzaldehyde and similarly when the mercury residue is replaced by iodine, the iodo-ra-hydroxy- benzaldehyde produced is convertible, by heating with sodium- hydroxide solution, into 2 : 3-dili3'droxybenzoic acid. This work has now been extended to the nitro- and nitrohydroxy- benzaldehydes. None of the three mononitrobenzaldehvdes yields mercury derivatives even when boiled in solution with mercuric acetate for three weeks. The m-compound when boiled with mercuric acetate and sodium hydroxide is oxidised to m-hydroxybenzoic acid, m. p. 140—143° (corr.) [aniline salt, m. p. 115—116° (corr.)]. The nitrohydroxybenzaldehydes f on the contrar}^ are readily mercurated. 3-Nitro-4-hydroxybenzaldehyde when boiled in 50 j)er cent, alcoholic solution with one molecular proportion of mer¬ curic acetate yields only 5-hydroxymercuri-3-nitro-4-hydroxy- benzaldehyde. The three known mononitro-3-hydroxybenz- aldeh\Tdes each yield both mono- and di-mercuri-derivatives, which * The melting point of 3 : 5-diacetoxydimercurisalicylaldehyde by a clerical error was given as 133° (decomp.) instead of 233° (decomp.; corr.}- in the previous paper. t The mercuration of nitro-o-hydroxybenzaldehydes has already beer, investigated by Whitmore and Middleton (J. Amer .Chern. Soc., 1923, 45, 1.53;.
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