Ethyl Acetate → HCID 58838600, compound

Participants

Reaction Steps

To a 500 ml round bottom flask equipped with a stir-bar was added crude 5-tert-butyl-2,3-dimethyl-benzene-1,4-diol as a solution in MeCN (200 ml). To the stirring solution at room temperature was added CAN (114 g, 220 mmole) as a solution in water (200 ml) in one portion. The biphasic reaction mixture was stirred vigorously at room temperature for one hour, after which time no further reaction was detected by TLC analysis (20% EtOAc:heptane). The reaction mixture was poured into MTBE (500 ml). The organic layer was separated, then washed with water until the aqueous phase remained colorless (3×200 ml). The solution was then washed with brine (2×200 ml), dried over sodium sulfate, and concentrated to a red oil. A portion of the crude product was further purified by silica gel chromatography (120 g, 0-20% EtOAc:heptane) to give 5-tert-butyl-2,3-dimethyl-[1,4]benzoquinone (213) as a volatile yellow oil. 1H NMR (400 MHz; C6D6; ppm): 6.42 (s, 1H), 1.66 (q, J=1.2 Hz, 3H), 1.61 (q, J=1.2 Hz, 3H), 1.12 (s, 9H).

Provenance & Evidence