Water → 5,7-Dihydroxy-2-methylthiochromone

HRID 1779521Notes

Reaction equation

HRID 1779521 reaction equation
Cl.CO.COC[O:7][C:8]1[CH:17]=[C:16]([O:18]COC)[CH:15]=[C:14]2[C:9]=1[C:10](=[S:23])[CH:11]=[C:12]([CH3:22])[O:13]2.O>C1COCC1>[OH:7][C:8]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]2[C:9]=1[C:10](=[S:23])[CH:11]=[C:12]([CH3:22])[O:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 21893726Hydrochloride methanolHCID 570855075,7-Bis(methoxymethoxy)-2-methylthiochromone

Product 1

HCID 1361024115,7-Dihydroxy-2-methylthiochromoneYield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under cooling on ice, 70 ml HCl-methanol was added to 70 ml of 9.47 g (30.35 mmol) 5,7-bis(methoxymethoxy)-2-methylthiochromone in THF. The mixture was stirred overnight at room temperature. Subsequently, water was added to the solution thus reacted. The product was extracted twice with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled out under reduced pressure, whereby 6.88 g of 5,7-dihydroxy-2-methylthiochromone was obtained. This product was used without being purified in the following reaction.

Workup

  1. customthus reacted
  2. extractionThe product was extracted twice with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-a7353647aa0a4a89ba2ac9e62f0419bd
Source dataset
uspto-grants-1997_05
Patent number
US05627204

Reaction notes

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