Sesamol → Ethanone, 1-(6-hydroxy-1,3-benzodioxol-5-yl)-

Temperature

90 °C

A solution of sesamol (5.6 g, 40 mmol) in acetic anhydride (20 mL) was cooled to 0° C. under an argon atmosphere. The solution was slowly added with boron trifluoride/diethyl ether complex (10 mL), and then the mixture was stirred at 90° C. for 2 hours. The reaction mixture was added to saturated aqueous sodium acetate (50 mL), and the mixture was stirred at room temperature. The solid formed was removed by filtration, and then the reaction mixture was extracted with ethyl acetate, and the organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual solid was suspended in methanol, thereby washed, then collected by filtration and dried to obtain 1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethanone (5.9 g, 82%).

1. additionThe solution was slowly added with boron trifluoride/diethyl ether complex (10 mL)
2. stirringthe mixture was stirred at room temperature
3. customThe solid formed
4. customwas removed by filtration
5. extractionthe reaction mixture was extracted with ethyl acetate
6. washthe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was evaporated under reduced pressure
9. washwashed
10. filtrationcollected by filtration
11. customdried

ORD record

ord-b1059b7d76534a23955b2b957c8ce9b2

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156827B2