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

Temperatur

-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-Eintrag

ord-c219d5993e1f45999b433bf4c6766c47

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08030504B2