6-Methoxy-1-tetralone 331 readily from a simple molecular still* connected to a pair of mercury pumps and heated by a bath at 120-125°. The colorless, non-viscous, water-soluble distillate (D,) weighed 1.8 g. Material possessing the same properties was obtained by treatment with an equivalent of aqueous (6 N) sodium hydroxide, removal of water by vacuum distillation, filtration to remove sodium chloride, and distillation from the molecular still. The liquid will be called D2.From Chloroacetone.-Five grams (0.055 mole) of chloroacetone and 0.16 mole of formaldehyde (as formalin) were mixed and maintained at 20°while 0.055 mole of 6 N sodium hydroxide solution was added little by little with stirring in the course of a day. The mixture was then heated to 60°for ten hours to consume the base. The water was removed by evaporation under reduced pressure up to 90°and sodium chloride was precipitated in quantitative yield. The sirupy material (6.5 g.) was not distillable in an ordinary Claisen flask up to 175°(bath) and 5 mm., but it came over readily from a molecular still with the conditions specified above. The limpid distillate, to be referred to as Dj, weighed 1.5-2 g. There was a redbrown, non-volatile residue in the still.Anal. Caled, for CjHioO,: active hydrogen atoms, 3. Found (Zerewitinoff): active hydrogen atoms from Dl( 3.13,3.09; from D3, 3.06, 2.98.F-Bromobenzoic Ester.-A mixture of 0.5 g. of acetylglycerol, 4 g. of F-bromobenzoyl chloride and 30 ml. of dry pyridine was maintained at 0°for thirty-six hours, and subsequently treated with 40 ml. of 5% sodium carbonate solution for eight more hours at 0°. Fifty grams of water was added, and the mixture was filtered. The acetylglycerol tris-F-bromobenzoate was digested in ethanol and recrystallized from butyl ether; yield of white needles, 2 g. (79%). D¡, D2 and D» all behaved (3) Hickman and Sanford, J. Phys. Chem., 34, 643 (1930).identically, giving products melting at 215-216°. Mixed melting point determinations of these products were not lowered.The same product was formed but in lower yield if a reaction temperature of 100-115°was maintained.Anal. Caled, for C2eHi»BrjC>7: Br, 35.1. Found: Br, 35.9. Reduction of Acetylglycerol .-Four grams of acetylglycerol was dissolved in 17 ml. of ethanol and 3 g. of water.
