Quinone → 4-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one

A mixture of 74 mg (1.3 mmol) of ground ammonium bifluoride (NH4HF2), 119 mg (1.1 mmol) of 1,4-benzoquinone, and 2 mL of acetonitrile was treated with 239 mg (1.3 mmol) of triethyltrifluoromethylsilane and stirred vigorously at room temperature for 4 hours. The mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates gave a black solid which was triturated with dichloromethane. The resulting mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates afforded a brown solid which was purified by PTLC (one 2 mm silica gel plate eluted with a 2% methanol-98% dichloromethane) to give 83 mg (42% yield) of 4-hydroxy-4-tri -fluoromethyl-2,5-cyclohexadien-1-one.

1. filtrationThe mixture was filtered
2. washthe filter cake was washed with dichloromethane
3. customConcentration of the combined filtrates gave a black solid which
4. customwas triturated with dichloromethane
5. filtrationThe resulting mixture was filtered
6. washthe filter cake was washed with dichloromethane
7. customConcentration of the combined filtrates afforded a brown solid which
8. customwas purified by PTLC (one 2 mm silica gel plate
9. washeluted with a 2% methanol-98% dichloromethane)

ORD record

ord-363bcfa0e090411e80a4107f80940251

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05008425