1,2-Dichloroethane → Potassium dobesilate

HRID 587813Notes

Reaction equation

HRID 587813 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].ClCCCl.[S:13](=O)(=[O:16])([OH:15])[OH:14].C(C(CCCC)C([O-])=O)C.[K+:28]>C(OCC)(=O)C>[K+:28].[OH:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[S:13]([O-:16])(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 23669619Potassium 2-ethylhexanoate

Product 1

HCID 23672329Potassium dobesilateYield 87.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
12.5 °C

Procedure

Hydroquinone (10 g, 0.09 mol) and 1,2-dichloroethane (30 mL) was taken in a round bottom flask, after cooling the flask to about 10-15° C., sulfuric acid (36 N, 8.9 g) was added dropwise at the same temperature and stirring continued further for about 10-15 min. Temperature was slowly raised to 40° C. then stirred for 3-8 h. The reaction mass was then cooled to 25-35° C. and ethyl acetate (100 mL) added to dissolve the solid formed. A solution of potassium 2-ethylhexanoate (18.2 g, 0.099 mol) in ethyl acetate (100 mL) was added slowly. The reaction was further stirred for an hour. The precipitated crude solid was filtered, washed with ethyl acetate to give 18 g of 2,5-dihydroxybenzenesulfonic acid potassium salt.

Workup

  1. temperatureTemperature was slowly raised to 40° C.
  2. stirringthen stirred for 3-8 h
  3. temperatureThe reaction mass was then cooled to 25-35° C.
  4. dissolutionto dissolve the solid
  5. customformed
  6. stirringThe reaction was further stirred for an hour
  7. customThe precipitated crude solid
  8. filtrationwas filtered
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-a9444ef7750145b88643ac8d7c49c5b9
Source dataset
uspto-grants-2016_01
Patent number
US09227928B2

Reaction notes

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