Acetylresorcinol → 3-Benzyloxyphenyl acetate

Resorcinol monoacetate (6.10 g, 40 mmol) in DMF (10 mL) was added dropwise to the mixture of NaH (95%, 0.92 g, 40 mmol) in DMF (50 mL). The mixture was stirred at room temperature for 10 min. Benzyl bromide (6.85 g, 40 mmol) in DMF (10 mL) was then added dropwise, and the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched slowly with water (100 mL) and then extracted with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the residue 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, J=1.2, 4.1 Hz), 7.27 (t, 1H, J=7.9 Hz), and 7.41 (m, 5H).

1. stirringthe mixture was stirred at room temperature for 2 h
2. customThe reaction mixture was quenched slowly with water (100 mL)
3. extractionextracted with ethyl acetate (3×100 mL)
4. washThe organic phase was washed with brine (2×50 mL)
5. dry with materialdried over Na2SO4
6. customThe solvent was removed in vacuo
7. customthe residue purified by flash column chromatography (1:1 hexane:methylene chloride)

ORD record

ord-a84357168fc64bf9842edb3355743c5d

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06034127