Benzenediazonium chloride → 3-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid

HRID 542944Notes

Reaction equation

HRID 542944 reaction equation
[Na].[OH:2][C:3]1[CH2:4][CH:5]([C:10]([OH:12])=[O:11])[CH2:6][C:7](=[O:9])[CH:8]=1.[Cl-].[C:14]1([N+:20]#[N:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[OH:2][C:3]1[CH2:4][CH:5]([C:10]([OH:12])=[O:11])[CH2:6][C:7](=[O:9])[C:8]=1[N:21]=[N:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 60992Benzenediazonium chlorideHCID 5360545SodiumHCID 144923703-Hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid

Product 1

HCID 1355835033-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.8 g. of sodium were dissolved in 900 ml. of methanol and to this solution were added 46.8 g. of 3-hydroxy-5-keto-3-cyclohexene-carboxylic acid. The resulting mixture was stirred, maintained between -4° C. and -8° C. by means of a cooling bath and treated over a period of 30 minutes with a phenyl-diazonium chloride solution (prepared from 27.9 g. of aniline, 450 ml. of water, 72 ml. of concentrated hydrochloric acid and 21.0 g. of sodium nitrite in 90 ml. of water). The resulting mixture was stirred for an additional hour at -5° C. to -10° C. The precipitated red reaction product was removed by filtration with suction and washed with about 1000 ml. of water, whereby there was obtained 3-hydroxy-5-keto-4-phenylazo-3-cyclohexene-carboxylic acid having a melting point of 218° C.

Workup

  1. temperaturemaintained between -4° C. and -8° C. by means of a cooling bath
  2. stirringThe resulting mixture was stirred for an additional hour at -5° C. to -10° C
  3. customThe precipitated red reaction product was removed by filtration with suction
  4. washwashed with about 1000 ml

Sources & evidence

ORD record
ord-36975dd952ec4a07813dad97226cb97a
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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