Methanol → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

Into a reaction vessel were charged 2.1 liters of methyl isobutyl ketone, 665.2 g (4.0 mol) of 2-methyl-2-adamantanol and 607.29 g (6.0 mol) of triethylamine, and their temperature was elevated to 60° C. under stirring. To the mixture, a solution prepared by dissolving 434.55 g (4.8 mol) of acryloyl chloride in 0.4 liter of methyl isobutyl ketone was added dropwise. At the end of the dropwise addition, the temperature was reached about 80° C. with the reaction heat. The mixture was kept at 80° C. for 2 hours with stirring to complete the reaction. After cooling, 64.02 g (2.0 mol) of methanol was added dropwise to deactivate the unreacted acryloyl chloride while keeping the temperature below 40° C. Then, 3.3 liters of water was added thereto to wash the mixture, followed by separation of the mixture into layers. Thereafter, 2.8 liters of a saturated aqueous sodium chloride solution was added to the organic layer to wash it again, and the mixture was separated into layers. To the organic layer after separation was added 204 g of active carbon “Carborafin” manufactured by Takeda Chemical Industries, Ltd. and stirred for 1 hour. The mixture was filtered thereafter and the residue was washed with 2 liters of methyl isobutyl ketone. The filtrate and the washing effluents were combined and concentrated at a bath temperature of 45° C. to obtain 886.17 g of crude 2-methyl-2-adamantyl acrylate.

1. customwas elevated to 60° C.
2. customTo the mixture, a solution prepared
3. additionwas added dropwise
4. additionAt the end of the dropwise addition
5. customwas reached about 80° C. with the reaction
6. temperatureheat
7. stirringwith stirring
8. customthe reaction
9. temperatureAfter cooling
10. customthe temperature below 40° C
11. washto wash the mixture
12. customfollowed by separation of the mixture into layers
13. additionThereafter, 2.8 liters of a saturated aqueous sodium chloride solution was added to the organic layer
14. washto wash it again
15. customthe mixture was separated into layers
16. customTo the organic layer after separation
17. additionwas added 204 g of active carbon “Carborafin”
18. stirringand stirred for 1 hour
19. filtrationThe mixture was filtered
20. washthe residue was washed with 2 liters of methyl isobutyl ketone
21. concentrationconcentrated at a bath temperature of 45° C.

ORD record

ord-9656dd680b02430b83ec06f663f5ba45

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06344582B1