Water → 1-[2-(Benzyloxy)phenyl]ethan-1-one

Temperature

0 °C

To a cold (0° C.) solution of 3-benzyloxypicolinonitrile (2.50 g, 11.9 mmmol) in tetrahydrofuran (100 mL) was added dropwise 0.92M methyl magnesium bromide in tetrahydrofuran (150 mL, 138 mmol). The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hrs. The reaction mixture was poured into water (2000 mL) and acidified with 10% sulfuric acid (500 mL). After being stirred for 30 min, the reaction mixture was poured into saturate aqueous NaHCO3 solution slowly and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, filtrated, and evaporated. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3) to give 1-(2-benzyloxy-phenyl)-ethanone as a colorless oil (2.49 g, yield; 92%).

1. waitat room temperature for 4 hrs
2. stirringAfter being stirred for 30 min
3. additionthe reaction mixture was poured
4. concentrationinto saturate aqueous NaHCO3 solution slowly
5. extractionextracted with ethyl acetate
6. washThe organic phase was washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltrated
9. customevaporated
10. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3)

ORD record

ord-895f3b15a7fb4600ac84a504d81e5d90

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562811B1