Mercury compounds of hydroxybenzaldehydes / by Thomas Anderson and Thomas Marvel Sharp.

  • Thomas Anderson Henry
Date:
[1922.]
Catalogue details

Licence: Public Domain Mark

Credit: Mercury compounds of hydroxybenzaldehydes / by Thomas Anderson and Thomas Marvel Sharp. Source: Wellcome Collection.

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    colourless, crystalline powder consisting of minute, distorted cubes and melts at 133° (corr.) with decomposition. It is insoluble in most solvents, but dissolves in hot acetic acid and sparingly in acetal; with sulphuric acid it gives an orange coloration [Found : C = 20-01, 2004; H = 11)2, 177; Hg = 02*0. CnH10O6Hg2 (039‘2) requires C = 20*05; H = 1*56; Hg = 02*70 per cent.]. The substance dissolves in sodium hydroxide solution, forming a neutral yellow liquid from which carbon dioxide causes the separa¬ tion of a yellow precipitate of 3 : 5-dihydroxydimercurisalicylaldchyde, which darkens on heating, but does not melt up to 300° [Found : Hg = 72-00. C7H604Hg2 (555*2) requires Hg = 72*24 per cent.]. Dilute hydrochloric acid added to a solution of the sodium salt causes precipitation of 3 : 5-dichlorodimercurisalicylaIdehyde, which darkens at 200°, sinters at 270°, but does not melt up to 310° [Found : Hg = 07*75 per cent. C7H402Cl2Hg2 (592-1) requires Hg = 07*74 per cent.]. On shaking the finely powdered diacetoxy-derivative with excess of a 10 per cent, solution of iodine in potassium iodide, it is almost immediately replaced by a yellow precipitate, which on recrystallisa¬ tion from methyl alcohol melts at 107*5° (corr.) [Found : C = 22*09; H = l*17; 1 = 07-79. C7H402I2 (373*8) requires 0 = 22-48; H = 107; I = 07-90 per cent.]. This di-iodo-compound is identical with 3 : 5-di-iodosalicylalde- hyde prepared by Seidel (J. pr. Chem., 1899, [ii], 59, 114) by the action of iodine on salicylaldeliyde in presence of mercuric oxide. A specimen thus prepared melted at 1075° and showed no depres¬ sion of melting point on admixture with the di-iodo-derivative prejiared from diacetoxydimercurisalicylaldehyde. The phenyl- hydrazone crystallises in yellow needles and melts at 172*5—173*5° (corr.). On oxidation with permanganate in acetone, the di-iodo- salicylaldchyde is converted into 3 : 5-di-iodosalicylic acid, m. p. 225J (decomp.; corr.) [Found: 1 = 05*73. C7H403I2 (389*8) requires I = 05*1 per cent.]. The mercury compound formed from salicylaldeliyde must there¬ fore be 3 : 5-diacetoxydimercuri-2-hydroxybenzaldehyde. The mother-liquor, which contains no free mercuric acetate, since it gave no precipitate with solution of sodium hydroxide or ammon¬ ium sulphide, was then poured into brine, when a voluminous, white precipitate formed, which, after washing with water, alcohol, and ether, and drying, contained ,04 per cent, of mercury, and appeared to be a mixture of chloromcrcuri- and dichlorodimercuri-salicyl- aldehydes: it was insoluble in the usual solvents, but on extraction with hot acetal there remained undissolved a pale pink, amorphous
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