Allyl Alcohol → 6-[(2-Propen-1-yloxy)methyl]-1,4-dioxane-2-methanol

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Reaction Steps

136 ml of allyl alcohol (2.0 mole, Aldrich) is stirred under nitrogen at room temperature and 0.25 g of sodium is added to the mixture and stirring continued for 2.5 hours. Then 13.1 g of 2,2'-(oxybismethylene)bisoxirane (0.1 mole) is added and the mixture then heated at reflux for 18 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with 2×200 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the resulting yellow oil then vacuum distilled through a 10 cm vigreux column. The fraction distilling at 120°-123° @ 0.4 mm is collected yielding 3.2 g (18%) of the above compound.

Provenance & Evidence