Sodium Hydroxide → Disodium

HRID 1708691Notes

Reaction equation

HRID 1708691 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[S:11]([OH:14])(=[O:13])=[O:12])([O-:3])=[O:2].Cl[O-].[Na+:17].[OH-:18].[Na+:19]>C(O)COCCO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([S:11]([OH:14])(=[O:12])=[O:13])[CH:6]=2)=[CH:6][C:5]=1[S:11]([OH:14])(=[O:12])=[O:13])([O-:2])=[O:18].[Na:17][Na:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 12332055p-Nitrotoluene-m-sulfonic acidHCID 23665760Sodium Hypochlorite

Product 2

HCID 141233DisodiumHCID 544603364,4'-Dinitrostilbene-3,3'-disulfonic acid

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

Combine p-nitrotoluene-m-sulfonic acid (5 g, 27 mmol) and diethylene glycol (30 mL) and warm to 40°-45° C. Add slowly to this with stirring, a mixture of sodium hypochlorite (5% available chlorine, 50 mL) and a solution of sodium hydroxide (6 g in 8 mL water). After addition, maintain the temperature at 50°-55° C. and stir for 35 minutes. Cool the reaction and filter to yield 4,4'-dinitrostilbene-3,3'-disulfonic acid, disodium salt. Convert this to the diacid by treatment with 1M hydrochloric acid, filter and concentrate under vacuum to yield 4,4'-dinitrostilbene-3,3'-disulfonic acid.

Workup

  1. additionAdd slowly to
  2. additionAfter addition
  3. temperaturemaintain the temperature at 50°-55° C.
  4. stirringstir for 35 minutes
  5. temperatureCool
  6. customthe reaction
  7. filtrationfilter

Sources & evidence

ORD record
ord-e53b3f308f794a4999ff1d1837fb584a
Source dataset
uspto-grants-1994_10
Patent number
US05359131

Reaction notes

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