Benzene → 6-Phenylhexanenitrile

A solution of 50.0 g (.284 mole) of 6-bromocapronitrile in 550 ml of benzene was cooled to 5° C. and to this was added 77.3 g (.580 mole) of anhydrous aluminum chloride in portions over a 10 minute period. The ice bath was removed and the vigorously stirred mixture was warmed slowly to reflux. After 2 hours at reflux, the mixture was cooled to room temperature, then poured slowly into a mixture of 50 ml of concentrated hydrochloric acid and 250 ml of ice water. The layers were separated and the aqueous portion was extracted twice with 125 ml portions of ether. The combined organic extracts were washed with 100 ml of saturated sodium bicarbonate solution, 100 ml of saturated sodium chloride solution, then dried over sodium sulfate, filtered, and evaporated leaving 53 g of a crude red/brown oil. Distillation under reduced pressure afforded 42.4 g (86%) of the nitrile as a pale yellow oil, bp 136°-140° C./2.5 mm of Hg.

1. customThe ice bath was removed
2. temperaturethe vigorously stirred mixture was warmed slowly
3. temperatureto reflux
4. temperatureAfter 2 hours at reflux
5. additionpoured slowly into a mixture of 50 ml of concentrated hydrochloric acid and 250 ml of ice water
6. customThe layers were separated
7. extractionthe aqueous portion was extracted twice with 125 ml portions of ether
8. washThe combined organic extracts were washed with 100 ml of saturated sodium bicarbonate solution, 100 ml of saturated sodium chloride solution
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customevaporated
12. customleaving 53 g of a crude red/brown oil
13. distillationDistillation under reduced pressure

ORD record

ord-c0eee28a4db44a8caf985554c8bb086c

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04554276