Methanol → 2-Methyl-2-adamantyl methacrylate

Participants

Reaction Conditions

Reaction Steps

Into a reaction vessel were charged 116.41 g of tetrahydrofuran and 16.63 g (0.1 mol) of 2-methyl-2-adamantanol, and 21.56 g (0.2 mol) of methacryloyl chloride was poured thereto at -10° C. under stirring. To the mixture, 25.56 g (0.25 mol) of triethylamine was added dropwise and the resulting mixture was left as it was for 15 minutes. The mixture was heated up to 69° C., the refluxing temperature, and stirring was continued for 11 hours while maintaining the refluxing state to react the mixture. After cooling, 6.41 g (0.2 mol) of methanol was added dropwise at -10° C. to deactivate the unreacted methacryloyl chloride. Then, the mixture was diluted with 116.41 g of methy isobutyl ketone. To the mixture, 68.87 g of water was added to wash it and thereafter the mixture was separated into layers. To the organic layer was added 112 g of a saturated aqueous sodium chloride solution. The resulting mixture was neutralized, under ice cooling, with a 5% aqueous sulfuric acid solution so as to adjust pH to from 7 to 8 and thereafter the mixture was separated into layers. The organic layer after separation was concentrated at a bath temperature of 40° C. to yield 23.62 g of brown crude 2-methyl-2-adamantyl methacrylate.

Provenance & Evidence