Triethylamine → HCID 59166788, compound

Analogously to L. Angiolini et al., 2000, Macromol. Chem. Phys. 201, 2646, a mixture of 10 mmol (1.82 g) of 10-hydroxycamphorquinone, 10 mg of 2,6-di-tert.butyl-4-methylphenol (inhibitor), 1.5 ml of dry triethylamine (TEA) and 50 ml of absolute 1,4-dioxane, under argon and with exclusion of daylight, was added dropwise at 0° C. to a stirred solution of 11 mmol (1.15 g) of methacrylic acid chloride, dissolved in 20 ml of 1,4-dioxane. There followed stirring for 2 h at room temperature and 2 h under reflux. The reaction mixture was filtered off from the formed TEA-HCl, diluted with diethyl ether, washed with 5% sodium bicarbonate solution and with water. After drying over anhydrous Na2SO4 the solution was concentrated to dryness in a rotary evaporator and the solid crude product recrystallized from toluene/n-hexane (20:80 v/v). 1.55 g (62% of the theory) of yellow crystals of 10-methacryloyloxycamphorquinone MACQ was obtained.

1. temperatureunder reflux
2. filtrationThe reaction mixture was filtered off from the formed TEA-HCl
3. additiondiluted with diethyl ether
4. washwashed with 5% sodium bicarbonate solution and with water
5. dry with materialAfter drying over anhydrous Na2SO4 the solution
6. concentrationwas concentrated to dryness in a rotary evaporator
7. customthe solid crude product recrystallized from toluene/n-hexane (20:80 v/v)

ORD record

ord-0bcd48f1e6dc4be3a1131b0f2b92cdd4

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659324B2