p-Acetylphenyl acetate → 4-(2-Hydroxypropan-2-yl)phenol

To a solution of 4-acetylphenyl acetate (250 mg, 1.4 mmol) in anhydrous THF (5 mL) cooled to −10° C. under nitrogen was added 3M methylmagnesium chloride solution in THF (2.81 mL, 8.42 mmol) over 10 minutes, keeping the internal temperature below −5° C. The resulting pale yellow solution was allowed to warm to room temperature for 5 hours. The reaction mixture was cooled in an ice bath and quenched with saturated aqueous ammonium chloride solution (20 mL). The resulting clear solution was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The solid residue was purified by silica gel column chromatography eluting with 10-50% EtOAc in heptanes to afford the title compound as white solid (100 mg, 47%).

1. customthe internal temperature below −5° C
2. temperatureThe reaction mixture was cooled in an ice bath
3. customquenched with saturated aqueous ammonium chloride solution (20 mL)
4. extractionThe resulting clear solution was extracted with EtOAc (2×50 mL)
5. washThe combined organic extracts were washed with brine (50 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe solid residue was purified by silica gel column chromatography
10. washeluting with 10-50% EtOAc in heptanes

ORD record

ord-8582f803d4ea487799aa8657fb520c0e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067922B2