3-Isopropylsalicylic acid → 1-[2-Hydroxy-3-(propan-2-yl)phenyl]ethan-1-one

Temperature

-75 °C

2-Hydroxy-3-isopropylbenzoic acid (Aldrich, 4.0 g, 22.2 mmol) was dissolved in tetrahydrofuran (20 mL), chilled to −75° C., and methyllithium (1.6M in diethyl ether, 42 mL, 66.6 mmol) was added. The mixture stirred overnight at ambient temperature. The mixture was quenched with methanol (50 mL), concentrate under reduced pressure, and ethyl acetate (200 mL) was added. The mixture was washed with 1N hydrochloric acid (200 mL), water (200 mL), and brine and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrate under reduced pressure. The residue was chromatographed on silica gel eluting with 0-to-30% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.23 (d, 6H), 2.64 (s, 3H), 3.39 (m, 1H), 6.87 (t, 1H), 7.41 (dd, 1H), 7.59 (dd, 1H), 12.69 (s, 1H). MS (DCI) m/z 179.07 (M+H)+.

1. customThe mixture was quenched with methanol (50 mL)
2. concentrationconcentrate under reduced pressure, and ethyl acetate (200 mL)
3. additionwas added
4. washThe mixture was washed with 1N hydrochloric acid (200 mL), water (200 mL), and brine
5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrate under reduced pressure
8. customThe residue was chromatographed on silica gel eluting with 0-to-30% ethyl acetate in hexane

ORD record

ord-1e32a1a539774a10b03ef3d219fff577

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08350083B2