Catechol → 4-Sulfopyrocatechol

HRID 1448971Notes

Reaction equation

HRID 1448971 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[S:9](=O)(=[O:12])([OH:11])[OH:10].C(=O)([O-])[O-].[Ba+2]>>[OH:2][C:1]1[CH:8]=[C:7]([S:9]([OH:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[OH:4]

Participants

4

Reactant 3

HCID 289CatecholHCID 1118Sulfuric AcidHCID 10563Barium Carbonate

Product 1

HCID 1890034-Sulfopyrocatechol

Conditions

Temperature
45 °C

Procedure

Catechol (180 g.) was added in portions to stirred sulfuric acid (138.5 ml.) so that the reaction temperature remained below 25° C. After addition was complete, the semi-solid mixture was heated at 45° C. for 60 minutes then cooled to room temperature and poured into ice-water (700 ml.). The solution was neutralized with solid barium carbonate, the barium sulfate collected, the filtrate acidified to pH 1 with concentrated sulfuric acid then refiltered. The filtrate was evaporated to leave crude 3,4-dihydroxybenzenesulfonic acid (182.40 g.) which was used without purification.

Workup

  1. customremained below 25° C
  2. additionAfter addition
  3. temperaturethen cooled to room temperature
  4. customthe barium sulfate collected
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-717b63f7914d4a838f94686c302365ef
Source dataset
uspto-grants-1980_02
Patent number
US04188390

Reaction notes

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