Toluene → (2-Hydroxymethyl-2-adamantyl)-methyl methacrylate

Participants

Reaction Steps

A mixture of 100 g of 2,2-adamantane dimethanol, 48.2 g of methacrylic acid, 20 g of toluene, 25 g of acidic ion-exchange resin Amberlist-15, and 0.1 g of 2,2′-methylenebis(6-t-butyl-p-cresol) was heated at 120° C. for 6 hours while the water being formed was azeotroped off. After the reaction mixture resumed room temperature, it was filtered through Celite. The filtrate was concentrated in vacuum. 300 g of hexane was added to the concentrate for recrystallization. The crystals were recovered and dried in vacuum, obtaining 45.0 g (yield 33%) of the target compound. The spectral data of this compound were identical with those of the product in Synthesis Example 1-2.

Provenance & Evidence