Partial Deuterium Labeling of Dimethacrylate Monomers

摘要

Methacrylic acid-d_5 was prepared in a yield of 30% with 98.6% deuterium incorporation using a two step synthesis.A solution of acetone-d_6 and KCN in D_2O was treated with glacial acetic acid to give the cyanohydrin of acetone-d_6.The latter compound was then dehydrated in anhydrous sulfuric acid at 120 deg C and subsequently hydrolysed in water at 90 deg C to form methacrylic acid-d_s.Hydrolysis of commercial nonaethyleneglycol dimethacrylate gave a mixture of ethylene glycols.These glycols were combined with methacrylic acid-d_5 in the presence of p-TsOH in benzene to form nonaethyleneglycol dimethacrylate-d_(10) with approx 21% deuterium incorporation.Deuterated bisGMA was also prepared from methacrylic acid-d_5 and diglycidyl ether of bisphenol-A.