Preparation of allyl alcohol-1,1-d2
6 g of lithium aluminum deuteride are made into a slurry with 300 ml of dry ether, cooled in an ice-bath, and treated with stirring with 20 g of acryloyl chloride in 100 ml of dry ether at such a rate that the temperature does not rise aboye 5° C. The mixture is stirred for 2 hours at room temperature and then cooled again to 0° C. The complex is decomposed by dropwise addition 7 ml of water, 7 ml of 15% sodium hydroxide solution, and further 7 ml of water, and the precipitate formed is filtered off and washed thoroughly with ether. The ethereal solutions are combined, dried over sodium sulfate, concentrated to 60 ml by distillation through a filled column, and again dried. 30 ml of dibutyl ether are then added and the mixture is fractionated through a semimicro column containing glass fragments. The fraction of b.p. 95-98° C is collected yielding 5.9 g of allyl alcohol-1,1-d2.
J. Org. Chem., 24, 297 (1959).