Methanol → 2-Methyl-2-adamantyl methacrylate

Participants

Reaction Steps

Into a reaction vessel were charged 598.54 g of methyl isobutyl ketone and 74.82 g(0.45 mol) of 2-methyl-2-adamantanol, and 72.75 g (0.675 mol) of methacryloyl chloride was poured thereto at room temperature under stirring. To the mixture, 82.79 g (0.81 mol) of triethylamine was added dropwise and the resulting mixture was left as it was for 15 minutes. The mixture was heated up to 80° C. and kept at this temperature for 24 hours under stirring. After cooling, 14.42 g (0.45 mol) of methanol added dropwise to deactivate the unreacted methacryloyl chloride while keeping the temperature below 10° C. Then, 223 g of water was added to wash the mixture and thereafter the mixture was separated into layers. To the organic layer, 112 g of a saturated aqueous sodium chloride solution was added, the resulting mixture was neutralized with a 5% aqueous sulfuric acid solution so as to adjust pH to from 7 to 8. Thereafter, the mixture was separated into layers. The organic layer after separation was concentrated at a bath temperature of 40° C. to yield 109.93 g of brown crude 2-methyl-2-adamantyl methacrylate.

Provenance & Evidence