Ammonium cerium (IV) nitrate → 2-Chloromethyl-3,5,6-trimethyl-[1,4]benzoquinone

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Reaction Steps

0.8 g (3.5 mmol) of 2-chloromethyl-3,5,6-trimethylhydroquinone dimethylether was dissolved in 20 mL of acetonitrile. After addition of 9.6 g of ammonium cerium (IV) nitrate in 200 mL of water to the solution, the mixture was extracted with ethyl acetate (100 mL and 50 mL). The combined extract dried over magnesium sulfate and the solvent was removed under reduced pressure. 50 mL of water was added to the residue and then the mixture was extracted with ethyl acetate (50 mL). The extract was washed with saturated NaCl solution (100 mL). The extract dried over magnesium sulfate and the solvent was removed under reduced pressure to give 2-chloromethyl-3,5,6-trimethylbenzoquinone as a yellow crystal. 1H NMR (300 MHz, CDCl3): 4.47 (s, 2H), 2.16 (s, 3H), 2.06 (s, 3H), 2.05 (s, 3H). ESMS: Calc. for C10H11ClO2 : 198.65; Found: 199.6 (M+H)+.

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