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

Participants

Reaction Steps

Into a reaction vessel were charges 33.26 g of methyl ethyl ketone, 16.63 g (0.1 mol) of 2-methyl-2-adamantanol and 30.36 (0.3 mol) of triethylamine, and their temperature was elevated to 60° C. under stirring. To the mixture, a solution prepared by dissolving 13.58 g (0.15 mol) of acryloyl chloride in 16.63 g of methyl ethyl ketone was added dropwise. At the end of dropwise addition, the temperature was reached 77° C. and the mixture was boiling with the reaction heat. The mixture was kept in a boiling state for 3 hours with stirring to complete the reaction. After cooling, 3.20 g (0.1 mol) of methanol was added dropwise to deactivate the unreacted acryloly chloride while keeping the temperature below 40° C. Then, 103 g of water was added to wash the mixture and thereafter the mixture was separated into layers. To the brown organic layer, 10 g of active carbon (Carborafin) was added and stirred. The mixture was thereafter filtered and the residue was washed with methyl ethyl ketone. The filtrate and washing effluents were combined and concentrated at a bath temperature of 45° C. to obtain 21.68 g of reddish orange crude 2-methyl-2-adamantyl acrylate.

Provenance & Evidence