HCID 19759911, compound → HCID 19759872, compound

HRID 1586865Notes

Reaction equation

HRID 1586865 reaction equation
[S:1]1[C:5]2S[CH2:7][CH2:8][C:4]=2[CH:3]=[C:2]1[C:9]([OH:11])=[O:10].O[O:13][S:14]([O-:16])=O.[K+]>O>[S:1]1[C:5]2[S:14](=[O:16])(=[O:13])[CH2:7][CH2:8][C:4]=2[CH:3]=[C:2]1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 19759911HCID 19759911, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 19759872HCID 19759872, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4,5-Dihydrothieno[2,3-b]thiophene-2-carboxylic acid (88.3 g, 0.474 mol) was added to a solution of Oxone® (730 g, 1.18 mol) in water (3.0 L), and the resulting suspension heated on a steam bath for 1 hour. During this time the solids dissolved to give a clear yellow solution. The reaction was cooled to 60° C. and filtered. The filtrate was extracted four times with ethyl acetate (6 L total) and the combined extracts washed with saturated brine and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo to give the title compound as a yellow solid (70 g, 68%). Recrystallization from dichloroethane gave an off-white powder, mp=227°-230° C. Anal. Calc. for C7H6O4S2 : C, 38.52; H, 2.77. Found: C, 38.53; H, 2.61.

Workup

  1. temperaturethe resulting suspension heated on a steam bath for 1 hour
  2. dissolutionDuring this time the solids dissolved
  3. customto give a clear yellow solution
  4. filtrationfiltered
  5. extractionThe filtrate was extracted four times with ethyl acetate (6 L total)
  6. washthe combined extracts washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff5d46ff51a046d796efe960f468e37d
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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