Phenol → Phenolindophenol

Beteiligte Stoffe

Reaktionsschritte

To prepare the starting material N,N-Dimethylindo-aniline (Phenol Blue III)--A solution of 0.075 mole of phenol, 4 g (0.1 mole) of sodium hydroxide, and 8 g (0.06 mole) of sodium acetate in 250 c.c of water was stirred mechanically in a salt-ice bath in such a way as to maintain a temperature of 0° to 5° during the reaction. Two dropping funnels were put in place, one containing 100 cc (0.1 mole) of 5% sodium hypochlorite, the other a solution of 0.05 mole of p-aminodimethylaniline hydrochloride in 100 cc of water. The two solutions were then added simultaneously in the course of forty-five to sixty minutes. The solution became blue after the addition of a few drops of the reagents and the dye soon began to separate. Stirring was then continued for fifteen minutes after completion of the addition and the product was then collected and washed several times with water; the dark blue filtrate, probably containing phenol-indophenol formed by alkaline hydrolysis of the product was discarded. The crude dye was crystallized from ethyl acetate, giving fine, intense violet needles, m.p. 161° [as reported by Gnelm and Bots J. Prakt. Chem., 69:162 (1904)] Yield 7.2 g (63%). This is generally the method of Gnelm and Bots, Supra [see also Heller Ann 392:16 (1912) and Cohen and Phillips, Suppl. No. 74 U.S. Pub. Health Reports 1929].

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