Acetonitrile → HCID 66935830, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 ml round bottom flask was added 2,3,5-trimethyl-[1,4]benzoquinone (0.51 g, 3.4 mmole), oleic acid (1.0 g, 3.5 mmole), and silver nitrate (0.62 g, 3.6 mmole) in a 1:1 mixture of water and acetonitrile (100 ml). The solution was heated to 70° C. under argon and an aqueous solution of K2S2O8 (0.86 g, 3.9 mmole in 50 ml water) was added dropwise to the homogenous mixture over 2.5 hours using a syringe pump. The reaction was stirred at 70° C. for an additional 30 minutes after addition, then cooled to room temperature. To the reaction mixture was added MTBE (200 ml) and water (100 ml). The organic layer was separated, washed with water (2×100 ml), then brine (2×100 ml). The solution was dried over sodium sulfate and concentrated to a yellow oil. The crude product was further purified by silica gel chromatography (120 g, 0-30% EtOAc:heptane) to give pure 2-heptadec-8-enyl-3,5,6-trimethyl-[1,4]benzoquinone (211; 25.2 mg, 2%) as a yellow oil. 1H NMR (400 MHz; d6-DMSO; ppm): 5.32-5.30 (m 2H), 2.42-2.38 (m, 2H), 1.98-1.93 (m, 4H), 1.95 (s, 3H), 193 (s, 6H), 1.40-1.22 (m, 22H), 0.84 (t, J=7.2 Hz, 3H).

Provenance & Evidence