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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    powder, which proved to be 3 : 5-dichlorodimercurisaIicylaldehyde (see above) [Found : Hg = 67’47. C7H402Cl2IIg2 (592’1) requires Hg = 67*74 per cent.]. The acetal solution on cooling deposited a pink solid which contained 58 per cent, of mercury instead of 53*4 required for a monochloromercuri-compound, and so far the latter has not been obtained in a pure state. Reduction of the amount of mercuric acetate used in the initial reaction to one molecular pro¬ portion merely reduced the ratio of pure diacetoxy-compound to mixed chloro-compounds formed from 8 to 1 to 0*8 to 1. p - II ydroxybenzaldeliydc. The p-hydroxybenzaldehyde used was prepared by the method described in British Patent 161679, depending on the condensation of phenol with formaldehyde; a yield of 42*6 per cent, of the theoretical was obtained. 4 : 5-Anhydro- 3 - acetoxymercuri - 5 - hydroxymercuri - 4 - hydroxybenz- aldehyde (Formula I).—This substance results as already stated (p. 1055) from the application of the general method to ^-hydroxy- benzaldehyde. It occurs as a colourless, crystalline powder, which under the microscope is seen to be composed of masses of minute cubes, is insoluble in water and most organic solvents, and has no definite melting point [Found: 0=18*79, 18*31; H = 1*44, 1*47; Hg = 69*15. C9H604Hg2 (579*2) requires C = 18*64; H = 1*03; Hg = 69*24 per cent.]. On steam distillation, after decomposition by phosphoric acid, it yields 9*61 per cent, of acetic acid (C9HG04Hg2 requires acetic acid = 10*36 per cent.). Hot acetic acid dissolves this anhydro-sub- stance, converting it into 3 : S-diaceloxydimercuriA-hydroxybenzalde- hyde, which separates as the solution cools in minute, colourless, glistening plates. This, like the anhydro-compound, darkens on heating but has no melting point up to 300° [Found : C = 20*74; Hg = 63*02. CnH10O6Hg2 (639*2) requires C = 20*65; Hg = 62*76 per cent.]. The diacetoxy-compound dissolves with difficulty in sodium hydroxide solution, yielding a slightly turbid solution, which could not be filtered clear. It is decomposed by carbon dioxide, yielding a dull grey precipitate of 3 : S-dihydroxydimercuriA-hydroxybenz- aldchyde [Found : Hg = 73*07. C7H604Hg2 (555*2) requires Hg = 72*24 per cent.], and by hydrochloric acid, giving the corresponding dichlorodimercuri-compound [Found : Hg = 67*07. C7H402Cl2Hg2 (592*1) requires Hg = 67*74 per cent.]. On shaking the finely-ground anhydro-compound with excess of iodine dissolved in potassium iodide solution, a pale yellow substance
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