Metalation of Alcohols and Amines 977 alcohol, the solution is filtered free from inorganic material, and subjected to complete distillation under reduced pressure at 40°. The residue is fractionated. The fraction boiling between 135-160°at 2-5 mm. consists chiefly of the hydroxy-lactone. It weighs 14 g. (35%). Fractionation at reduced pressure yields the pure lactone which boils at 145-148°at 2-4 mm.Preparation of Isocrotonolactone.-Seventy-one grams of phosphorus pentoxide is added, 10 to 20 g. at a time, to a solution of fifty grams of ß-hydroxybutyrolactone in 200 cc. of dioxane. The mixture is allowed to stand for an hour (in one experiment the mixture stood overnight without ill effect). The dioxane solution is then decanted into a Claissen flask. The residue is extracted twice with absolute alcohol, the alcohol extracts being added to the dioxane solution. The solvent is removed under reduced pressure (10-15 mm. with water-bath at 70-80°), and the residue is distilled at 7 mm.The boiling range of 22 g. of material obtained in this way was 80-86°(53%).
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