Phenol → Phenolindophenol

HRID 260017

反応式

HRID 260017 の反応式
CN([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[CH:17]=[CH:16][C:14](=[O:15])[CH:13]=[CH:12]2)=[CH:6][CH:5]=1)C.C1([OH:24])C=CC=CC=1.[OH-].[Na+].C([O-])(=O)C.[Na+].Cl[O-].[Na+].Cl.NC1C=CC(N(C)C)=CC=1>O>[CH:6]1[C:7](=[N:10][C:11]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)[CH:8]=[CH:9][C:4](=[O:24])[CH:5]=1

参加物

8

反応物 6

HCID 996PhenolHCID 77361,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 750784-((4-(Dimethylamino)phenyl)imino)-2,5-cyclohexadien-1-oneHCID 517045Sodium AcetateHCID 23665760Sodium Hypochlorite

生成物 1

HCID 10379Phenolindophenol

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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].

後処理

  1. temperatureto maintain a temperature of 0° to 5°
  2. customduring the reaction
  3. additionThe two solutions were then added simultaneously in the course of forty-five to sixty minutes
  4. customto separate
  5. waitwas then continued for fifteen minutes
  6. additionafter completion of the addition
  7. customthe product was then collected
  8. washwashed several times with water

出典と根拠

ORDレコード
ord-d494efb7307e4b4b838e6bf0b809c84e
出典データセット
uspto-grants-1996_06
特許番号
US05525480

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