Hydrogen Peroxide → Sodium 4-methoxy-2-(methoxycarbonyl)benzenesulfonate

HRID 1249461Notes

Reaction equation

HRID 1249461 reaction equation
S[C:2]1[CH:11]=[C:10](OC)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:14]([O-])=[O:15].[Na+:17].OO.[S:20]([O-:23])([O-:22])=[O:21].[Na+].[Na+]>C(O)=O>[CH3:14][O:15][C:9]1[CH:10]=[CH:11][C:2]([S:20]([O-:23])(=[O:22])=[O:21])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=1.[Na+:17]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 2723810Sodium FormateHCID 13769568Methyl 2-mercapto-4-methoxybenzoate

Product 1

HCID 23672128Sodium 4-methoxy-2-(methoxycarbonyl)benzenesulfonateYield 731.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 50 g of the compound of Example 2, 34 g of sodium formate and 505 ml of formic acid was warmed to 35° C. and 90 ml of 30% hydrogen peroxide was added slowly over 0.75 hours. The reaction temperature was allowed to warm to 55° C. and held at 55° C. for 2 hours. The reaction mixture was cooled to ambient temperature and 7 g of sodium sulfite was added in portions to destroy excess hydrogen peroxide. The reaction mixture was concentrated in vacuo at 50° C. Toluene (250 ml) was added to the residue, and the suspension was concentrated in vacuo. Repeating this procedure gave 109 g of the title compound as a moist white solid, m.p. >280° C.

Workup

  1. temperatureto warm to 55° C.
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customto destroy excess hydrogen peroxide
  4. concentrationThe reaction mixture was concentrated in vacuo at 50° C
  5. additionToluene (250 ml) was added to the residue
  6. concentrationthe suspension was concentrated in vacuo

Sources & evidence

ORD record
ord-6bcc6fa24b234ccda3f0cd02fd880260
Source dataset
uspto-grants-1986_12
Patent number
US04632693

Reaction notes

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