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Halogen-Metal Interconversions 1843After three days the reaction was complete and the alcohol removed under reduced pressure in an atmosphere of nitrogen, leaving a brownish, highly viscous residue of 24.9 g. This contained some diol which was estimated by catalytic hydrogenation and found to be 20.5%. On the basis of the cyclopentadiene used, the yield of the diol was 20.7% and that of the tetrol 60.9%.To remove the diol, the mixture was extracted a number of times with anhydrous ethyl acetate in which the tetrol is insoluble. Finally, the tetrol was precipitated a number of times from ethyl alcohol by the addition of ethyl acetate. This procedure yielded an amorphous, slightly colored and extremely hygroscopic solid which could not be crystallized. It had no definite m. p., turning brown at 190°and black at 200 °. It is very soluble in water and alcohol but insoluble in ether, ethyl acetate and hydrocarbon solvents. Attempts to distil it at a very high vacuum caused decomposition and the product formed was no longer soluble in water.The tetrabenzoate was prepared by shaking a mixture of tetrol (0.5 g.) in water (5 cc.) with benzoyl chloride (3 cc.) and 10 cc. of 10% sodium hydroxide solution. The oil which separated was extracted with ether, the ethereal solution washed with dilute sodium hydroxide, dried with anhydrous magnesium sulfate and the ether removed.A viscous liquid was obtained which failed to crystallize.