Hydrochloric Acid → 1-Chloro-2,6-diethyl-4-methylbenzene

Participants

Reaction Conditions

Reaction Steps

To an initial charge of 65 ml of 36% aqueous HCl are added, in portions, 16.33 g [0.1 mol] of 2,6-diethyl-4-methylaniline. The resulting thick suspension is stirred at 65° C. for 5 minutes. It is then cooled to −10° C., and a solution of 8 g [0.116 mol] of NaNO2 in 35 ml of water is added dropwise within approx. 1 h at such a rate that the temperature does not exceed −5° C. 80 mg of sulphamic acid are added. Then the suspension of the diazonium salt, cooled to −10° C., is metered within about 30 minutes into a solution, heated to 70° C., of 8.36 g [0.05 mol] of FeCl3 in 65 ml of 36% aqueous HCl. The reaction mixture is then stirred at 65-75° C. for another 1 hour, allowed to cool to room temperature and admixed with 200 ml of water, the phases are separated and the aqueous phase is extracted three times with 50 ml each time of methylene chloride. The combined organic phases are washed twice with 25 ml each time of water, dried and concentrated under reduced pressure. This gives 18.1 g of an oil which, according to GC, contains 89% 2,6-diethyl-4-methylchlorobenzene (88% of theory).

Provenance & Evidence