Potassium Carbonate → HCID 10654815, Verbindung

Temperatur

150 °C

To 200 ml of a solution of 17.4 g of 3,6-dimethylsalicylaldehyde in N,N-dimethyformamide were added 32 g of anhydrous potassium carbonate and 17.8 ml of bromoacetaldehyde diethyl acetal. The resulting mixture was stirred at 150° C. for 2.5 hours, cooled to room temperature by allowing to stand, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to give 23.4 g of an ether. This ether was dissolved in 120 ml of acetic acid. The resulting solution was refluxed under nitrogen stream for 8 hours, cooled to room temperature by allowing to stand, and poured into a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting crude product was washed with hexane to give 7.8 g of the title compound as a pale yellow solid.

1. temperaturecooled to room temperature
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated
6. customThe resulting residue was purified by silica gel column chromatography
7. customto give 23.4 g of an ether
8. temperatureThe resulting solution was refluxed under nitrogen stream for 8 hours
9. temperaturecooled to room temperature
10. extractionThe resulting mixture was extracted with ethyl acetate
11. washThe organic layer was washed with brine
12. dry with materialdried over anhydrous magnesium sulfate
13. customthe solvent was evaporated
14. washThe resulting crude product was washed with hexane

ORD-Eintrag

ord-7e025ebcd324481bbee0db56e7ab308a

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06358995B1