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Vol. 57 sulfonate was heated on a water-bath for two and one-half hours with stirring. The chloroethoxy compound was separated from unaltered ester by shaking with a minimum quantity of petroleum ether. The yield was 75%, and the compound melted at 64-65 °after crystallization from 95% ethanol.Anal. Caled, for Ci«Hu02C1: Cl, 14.38. Found: Cl, 14.53 and 14.51.4-|3-Diethylaminoethoxydibenzofuran, C12H7O [OCH2-CH2N(C2H6)2], was prepared in a 22% yield by heating the chloroethoxy compound with diethylamine at 100°f or eighteen hours. The impure base could not be distilled without significant decomposition. The hydrochloride formed by passing hydrogen chloride into a dry etheracetone solution precipitated as an oil which crystallized after standing for several days and melted at 128.5-129.5°o n crystallization from an ether-acetone solution.Anal. Caled, for CisH2202NCl: N, 4.38. Found: N, 4.32 and 4.48.4-|3-Piperidinoethoxydibenzofuran, 0 2 70(00 20 2-NC5H10), was prepared by heating the chloroethoxy compound with piperidine on a steam-bath for twenty-four hours. The yield was 52%. The free amine distils at 213°( 2 mm.) and the hydrochloride melts at 210.5-212°.Anal. Caled, for C,9H2202NC1: N, 4.22. Found: N, 4.44 and 4.56. 4-Dibenzofurancarboxylic AcidChloride, Ci2H7-OCOC1.-The 4-dibenzofurancarboxylic acid was prepared in 30% yield by carbonation of 4-dibenzofuryl-lithium (prepared, in turn, through «-butyl-lithium and dibenzofuran); and in 50% yield by carbonating 4-dibenzofurylsodium. A quantitative yield of the crude acid chloride was obtained from 112 g. (0.52 mole) of 4-dibenzofurancarboxylic acid and 500 g. (4.2 moles) of thionyl chloride.The acid chloride was crystallized from ethanol, and finally purified by sublimation to melt at 118°.

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