Acetylresorcinol → 3-Benzyloxyphenyl acetate

Resorcinol monoacetate (6.10 g, 40 mmol) in DMF (10 mL) was added dropwise to a mixture of NaH (95%, 0.92 g, 40 mmol) in DMF (50 mL). The reaction mixture was stirred at room temperature for 10 min. Benzyl bromide (6.85 g, 40 mmol) in DMF (10 mL) was added dropwise and stirring was continued at room temperature for 2 h. The reaction was quenched carefully with water (100 mL) and then extracted with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL), dried over Na2 SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a white solid (5.30 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 2.28 (s, 3H), 5.03 (s, 2H), 6.72 (m, 2H), 6.85 (dd, 1H), 7.27 (t, 1H), 7.41 (m, 5H).

1. stirringstirring
2. waitwas continued at room temperature for 2 h
3. customThe reaction was quenched carefully with water (100 mL)
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe organic phase was washed with brine (2×50 mL)
6. customdried over Na2 SO4
7. concentrationconcentrated in vacuo
8. customThe residue was then purified by flash column chromatography (1:1 hexane:methylene chloride)

ORD record

ord-7c40cba6b854474296734844174ab641

Source dataset

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05792769