Hydrochloric Acid → 2'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

To a mixture of 2′,6′-dihydroxyacetophenone (1 g), potassium carbonate (4.54 g) and benzyltri(n-butyl)ammonium chloride (0.41 g) in chloroform (13 mL) were added water (0.5 mL) and acetobromo-α-D-glucose (2.7 g), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and the mixture was acidified by addition of 2 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the extract was washed with water and brine. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was treated with methanol, and the precipitated crystals were collected by filtration and dried under reduced pressure to give the title compound (1.38 g).

1. extractionThe resulting mixture was extracted with ethyl acetate
2. washthe extract was washed with water and brine
3. dry with materialThe extract was dried over anhydrous magnesium sulfate
4. customthe solvent was removed under reduced pressure
5. additionThe residue was treated with methanol
6. filtrationthe precipitated crystals were collected by filtration
7. customdried under reduced pressure

ORD record

ord-9d240b3dce7d47339874ef7064ae6587

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566699B2