The ether was evaporated under reduced pressure and the sirupy residue taken up in alcohol. A small amount of amorphous solid separated and was removed by filtration. The alcoholic solution was poured into ether and the resulting solution washed thoroughly with water and then extracted with 5% sodium carbonate solution. The intensely red aqueous layer was separated and acidiiled and extracted with ether. The ether layer was washed with several portions of dilute ammonium carbonate solution, dried over sodium sulfate and evaporated to dryness. The yellow-brown, solid residue was extracted with 25 cc. of boiling xylene in several portions. The filtered xylene solution was allowed to stand for several days and slowly deposited a mixture of an amorphous yellow powder (40 mg.) and hard brown-yellow nodules (190 mg.). The nodules were partially purified by solution in cold, dilute aqueous-alcoholic sodium hydroxide followed immediately by precipitation with dilute hydrochloric acid. The pigment was thus obtained as brownish-yellow needles.
Bunte Salts for Syntheses of Aliphatic Disulfides 149 sodium bisulfite and finally with water. The residue from evaporation of the solvent was crystallized from chloroform in plates, m. p. 216-218°. A mixed melting point with an authentic sample of 3-hydroxy-efro-bilianic acid gave no depression. A yield of 110 mg. of pure product was obtained.
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