Sulfuric Acid → HCID 86739519, compound

HRID 1462126Notes

Reaction equation

HRID 1462126 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[OH-:26].[Na+].S(=O)(=O)(O)[OH:29]>O>[OH:26][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:29])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide2×HCID 54289261HCID 54289261, compound

Product 1

HCID 86739519HCID 86739519, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

25.6 kg of 4-chloro-3-nitrophenylmethylsulfone are stirred slowly into 4 kg of 30% aqueous sodium hydroxide and the mixture is diluted continuously with water to a volume of about 50 liters. The reaction mixture is heated to 90° C. and then a further 29 kg of 30% aqueous sodium hydroxide are added, with stirring, over 3 to 4 hours. The mixture is then heated for 90 minutes to 103° C. After it has cooled to about 60° C., the solution is adjusted with 16% sulfuric acid to a pH value of about 1.5, whereupon the product precipitates. The precipitate is isolated by filtration, washed and recrystallised from ethanol. Yield: 24 kg of colourless crystals with a melting point of 166°-168° C.

Workup

  1. temperatureThe mixture is then heated for 90 minutes to 103° C
  2. temperatureAfter it has cooled to about 60° C.
  3. customprecipitates
  4. customThe precipitate is isolated by filtration
  5. washwashed
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ad868a99a43746eb909e0086e6921fd1
Source dataset
uspto-grants-1984_07
Patent number
US04459152

Reaction notes

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