Hexachlorocyclopentadiene → 1,2,3,4,5-Pentachloro-5-ethylcyclopentadiene
Reaction equation
P(O[CH2:9][CH3:10])(OCC)OCC.[Cl:11][C:12]1(Cl)[C:16]([Cl:17])=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]1[Cl:20]>O>[Cl:11][C:12]1[C:16]([Cl:17])([CH2:9][CH3:10])[C:15]([Cl:18])=[C:14]([Cl:19])[C:13]=1[Cl:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of triethyl phosphite (182.8 g., 1.1 mole) in 200 ml. of petroleum ether (pentane range) was charged to the equipment of the preceding example, which was immersed into a rock-salt-ice mixture. When the temperature of the solution reached 0°C. hexachlorocyclopentadiene (272.8 g., 1.0 mole), dissolved in 100 ml. of light petroleum ether, was added slowly to the well stirred solution at such a rate that the temperature of the mixture did not exceed +5°C. The addition required 10 hours. The clear, brown solution was poured with good stirring into a 5 liter 3 neck flask containing 2 liters of water and, after 1 hour of stirring, the product was steam distilled. After the separation of the low boiling petroleum ether 1,2,3,4,5-pentachloro-5-ethyl-cyclopentadiene, completely free of any phosphorus compound, distilled over as a pale yellow heavy oil, nD25 1.5398, the infrared spectrum of which matched perfectly that of the previous example. The product weighed 257.0 g., which corresponds to a 96.4% yield.
Workup
- customreached 0°C.
- dissolutiondissolved in 100 ml
- customdid not exceed +5°C
- additionThe addition required 10 hours
- additionThe clear, brown solution was poured
- stirringafter 1 hour of stirring
- distillationdistilled
- customAfter the separation of the
- distillationcompletely free of any phosphorus compound, distilled over as a pale yellow heavy oil
Sources & evidence
- ORD record
- ord-0bbd3f1f77f84511872aa52b3e6648b7
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03933922
Reaction notes
Loading…