Acetone → HCID 71278892、化合物

2,5-Dihydroxy-3-methylbenzoic acid (4.7 g, 29 mmol) was added successively with acetone (40 mL), dimethyl sulfate (9.0 g, 71 mmol), and potassium carbonate (10 g, 72 mmol), and the mixture was stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure, the residue was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with acetone (50 mL), potassium carbonate (1.0 g, 72 mmol), and methyl bromoacetate (6.6 g, 43 mmol), and then the mixture was refluxed for 8 hours by heating. The reaction mixture was filtered through Celite, and then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50)) to obtain methyl 5-methoxy-2-(2-methoxy-2-oxoethoxy)-3-methylbenzoate (4.9 g, 63%).

1. customThe solvent was evaporated under reduced pressure
2. additionthe residue was added with ethyl acetate
3. washthe organic layer was washed successively with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. temperaturethe mixture was refluxed for 8 hours
7. temperatureby heating
8. filtrationThe reaction mixture was filtered through Celite
9. customthe solvent was evaporated under reduced pressure
10. dissolutionThe residue was dissolved in ethyl acetate
11. washthe organic layer was washed successively with water and saturated brine
12. dry with materialdried over anhydrous magnesium sulfate
13. customThe solvent was evaporated under reduced pressure
14. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50))

ORDレコード

ord-a59c6d46701d409aa99501e3d45fd110

出典データセット

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09156827B2