Hydrogen Peroxide → HCID 13187533, compound

Participants

Reaction Steps

1-(But-3-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene (5.08 g) in 50 mL THF was treated with 9-borabicyclo[3.3.1]nonane (9-BBN) (2.96 g) and stirred overnight at room temperature. A chilled solution of 10 M NaOH (10 mL) and 35% w/w H2O2 (10 mL) was added to cold borane (0° C.) such that the internal temperature never exceeded 36° C. The cloudy solution was stirred vigorously and treated with 2 g K2CO3 until the layers clarified. Isopropyl acetate (100 mL) was added followed by separation and extraction of the aqueous phase 3×60 mL isopropyl acetate. The combined organics were washed with 50 mL saturated NaCl, dried over Na2SO4 and concentrated to a pale yellow oil. Flash chromatography yielded 3.3 g of 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)butan-1-ol as a white powder (60.3%). Mp 85.1-87.1° C.; 1H NMR (400 MHz, CDCl3) δ=3.67 (m, 5H), 3.64 (s, 3 H), 2.63 (q, 2 H), 2.22 (s, 3 H), 2.17 (s, 6 H), 1.68 (m, 2 H), 1.55 (m, 2 H) ppm.

Provenance & Evidence