Predominantly para-substituted alkyltoluenes are formed in yields of 52–78% in the alkylation of toluene with alcohols in the presence of boron trifluoride at 170–180° under the pressure of 50–60 atm; the yield of dialkyltoluenes in these cases did not exceed 9–17%.
Yields of the alkyltoluenes depend on the molar ratios of the original reagents; at a molar ratio of toluene to alcohol equal to 1:2, the yields of alkyltoluenes are raised by 20–25%.
The isomerization of the secondary radicals is not observed in alkylating toluene with alcohols under pressure and under the conditions employed by us.
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Romadan, I.A., Grikit, É.Y. & Shuikin, N.I. Alkylation of toluene by molecular compounds of alcohols with boron trifluoride under pressure. Russ Chem Bull 8, 675–679 (1959). https://doi.org/10.1007/BF00915864
- Boron Trifluoride