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.

    9/16 (page 1161)
    5-Nitro-l-methoxy-2 :3-methylenedioxybenzene, OMe readily soluble in alcohol, ethyl acetate, or benzene, from each of which it crystallises in long, almost colourless needles. It may readily be sublimed when heated above its melting point. When warmed with alcoholic potash it is hydrolysed to the corresponding nitrophenol, 5-nitro-\-liydroxy-2 : 3-methylenedioxybenzene, which crys¬ tallises from water in yellow, silky needles melting at 94°, and is soluble in alkalis with a deep red colour. In determining the con¬ stitution of 5-nitro-l-methoxy-2 : 3-methylenedioxybenzene it was necessary, as already explained, to prepare successively myristicinoyl chloride, myristicinamide, and 5-amino-l-methoxy-2 : 3-methylene¬ dioxybenzene. Since these substances have not hitherto been described, the method of preparation, together with their characteristic properties, may briefly be indicated. Myristicinoyl Chloride, CTL^^j |GOCl.—^ mixture of myristi- OMe cinic acid (1 mol.) and phosphorus pentachloride (1 mol.) was heated for a short time at 100°. After removal of the phosphoryl chloride, the product was purified by distillation under diminished pressure. Myristicinoyl chloride distils at 189—190°/20 mm. as a colourless oil, which rapidly solidifies, and crystallises from a mixture of benzene and light petroleum in long, thin, colourless needles melting at 105°: 0-3236 gave 0-2200 AgCl. Cl =16-8. C9H704C1 requires Cl = 16-6 per cent. Myristicinamide, CH2<C CO-NIL -To a solution of myristi- OMe cinoyl chloride in benzene an excess of concentrated ammonia was added, and the mixture vigorously shaken. The precipitated amide was collected, and recrystallised from hot water, in which it is only moderately soluble. It separated in long, thin needles, which con¬ tain one molecule of water of crystallisation, and melts at 184°. It is readily soluble in hot alcohol, from which it is deposited in clusters of feathery needles : 0-7164 lost, at 105°, 0-0631 H20. H20 = 8-8. 0-1485 gave 0-3028 C02 and 0~0660 H20. C = 55-6 ; H = 4*9. C9II904N,H20 requires H20 = 8'5 per cent. C9H904N requires C = 55-4 ; H = 46 per cent.