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A solution of 272.8 g. (1.0 mole) of hexachlorocyclopentadiene in 300 ml. of petroleum ether (pentane range) was charged to a 2 liter 3 neck flask equipped with stirrer, thermometer, dropping funnel and an exit line protected with a drying tube. The flask was immersed in ice-water and triethyl phosphite (182.8 g., 1.1 mole) was added slowly from the dropping funnel at such a rate that the temperature of the reaction mixture did not exceed +15°C. After the addition was completed (which required 5 hours) the clear, brown solution was, after the stripping of the solvent, fractionated in vacuum through a 20 inch column, filled with glass helices. A lower boiling fraction, 161 g., b.p. 39°C. at 0.4 mm., nD25 1.4253 consisted of pure ethyl phosphorochloridate, Cl(EtO)2PO, which, accordingly, was obtained in 93.4% yield. Then the temperature rose fast in the column and a pale yellow oil distilled over sharply at 50°C. and 0.18 mm. Infrared and elemental analyses indicated that the yellow oil, nD25 1.5394, is pure 1,2,3,4,5-pentachloro-5-ethylcyclopentadiene.

1. customequipped with stirrer
2. customan exit line protected with a drying tube
3. customdid not exceed +15°C
4. additionAfter the addition
5. custom5 hours
6. additionfilled with glass helices
7. customaccordingly, was obtained in 93.4% yield
8. distillationa pale yellow oil distilled over sharply at 50°C.