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

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)+.

1. extractionthe mixture was extracted with ethyl acetate (100 mL and 50 mL)
2. extractionThe combined extract
3. dry with materialdried over magnesium sulfate
4. customthe solvent was removed under reduced pressure
5. addition50 mL of water was added to the residue
6. extractionthe mixture was extracted with ethyl acetate (50 mL)
7. washThe extract was washed with saturated NaCl solution (100 mL)
8. dry with materialThe extract dried over magnesium sulfate
9. customthe solvent was removed under reduced pressure

ORD record

ord-b37eeeb2b221401bb083a87fc9eb0fab

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05969133