Water → 5,7-Dihydroxy-2-methylthiochromone

HRID 1488786Notes

Reaction equation

HRID 1488786 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-8d97c6e1922647259d3fc9385837e509
Source dataset
uspto-grants-1997_10
Patent number
US05675023

Reaction notes

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