tert-Butanol → HCID 90409143, compound

Participants

Reaction Steps

To a solution of methyl 3-hydroxy-2-methyl-4-(prop-1-en-1yl)benzoate (1.66 g, 8.05 mol) in dioxane/water (280 mL 2.5/1 ratio) was added sodium periodate (3.96 g, 18.51 mmol) and 2.5 wt % solution of osmium tetroxide in tert-butanol (3.3 ml, 2.66 mmol). The reaction mixture was stirred overnight at room temperature. LCMS showed a single peak with the expected product mass. After aqueous work up and extraction with EtOAc, the crude product was purified on ISCO system (40 g silica gel column, hexane/EtOAc gradient) to get 1.2 g (77% yield) of the aldehyde. 1H NMR (400 MHz, CDCl3) δ 11.39 (s, 1H), 9.93 (s, 1H), 7.45 (d, J=8.1 Hz, 1H), 7.38 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.44 (s, 3H).

Provenance & Evidence