Water → 5,7-Dihydroxy-2-methylthiochromone

HRID 441054Notes

Reaction equation

HRID 441054 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 of hydrochloric acid/methanol was added to 70 ml of 9.47 g of 5,7-bis(methoxymethoxy)-2-methylthiochromone (30.35 mmol) in THF, and the mixture was stirred overnight at room temperature. After addition of water, the reaction solution was extracted twice with ethyl acetate, and the organic layer was washed with saturated NaCl water and dried over sodium sulfate anhydride. The solvent was distilled off under reduced pressure, to give 6.88 g of 5,7-dihydroxy-2-methylthiochromone. This product was subjected without purification to the following reaction.

Workup

  1. extractionthe reaction solution was extracted twice with ethyl acetate
  2. washthe organic layer was washed with saturated NaCl water
  3. dry with materialdried over sodium sulfate anhydride
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-02dbb046a21e4bbe9447cec56a50ad60
Source dataset
uspto-grants-1996_05
Patent number
US05521216

Reaction notes

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