Olah, George A. published the artcileFriedel-Crafts alkylation of anisole and its comparison with toluene. Predominant ortho-para substitution under kinetic conditions and the effect of thermodynamic isomerizations, Recommanded Product: 2-Isopropylanisole, the publication is Journal of the American Chemical Society (1984), 106(18), 5284-90, database is CAplus.
The AlCl3-, BF3-, and 65% HPF6-catalyzed Friedel-Crafts alkylation of anisole with alkyl halides and alcs. was examined The alkylation of anisole with lower catalyst concentrations under mild conditions shows predominant ortho/para directing effects hdgenerally with a ratio of ∼2:1, with the amount of meta isomer <3%. With swamping catalyst conditions the amount of meta substitution in methylation and ethylation can substantially increase. The isomer distribution in tert-butylation changes with time due to rapid ortho-para interconversion. Consequently, the AlCl3-catalyzed isomerization of isomeric alkylanisoles was also studied. In case of tert-butylanisoles, the ortho isomer shows relatively rapid conversion into para followed by much slower isomerization to meta. The para and meta isomers show isomerization to meta-para mixtures Isomerization of ethyl-, isopropyl-, and benzylanisoles is generally slow whereas methylanisoles do not isomerize. Comparing the alkylation results of anisole with those of toluene indicates that the latter are readily affected by concurrent (and in some cases consecutive) isomerization. As the barrier for isomerization in the benzenium ion intermediates of the alkylations is higher in the case of MeO- than Me-substituted systems, anisole tends to give the kinetically controlled ortho-para alkylation products and the amount of meta isomer is low. Study of alkylation of 3,5-di- and 2,4,6-trideuteriated toluene and anisole and comparing retained D contents with isomer distributions shows that alkylated product formation in the case of toluene, but not of anisole, is preceded by intramol. 1,2-alkyl, and H-D shifting, resulting also in increased meta substitution. This effect is most predominant in methylation and ethylation where the alkyl shifts are intramol. but not in tert-butylation and benzylation, where alkyl transfer is intermol. Isopropylation is intermediate in nature. No simple selectivity-reactivity relation is indicated in the alkylation reactions. As shown in benzylations with increasingly electron-donating and -withdrawing substituted benzyl chlorides, the overall rate (i.e., substrate selectivity) and isomer distributions (i.e., regioselectivity) are not determined in the same step, as significantly decreased substrate selectivity is not accompanied by loss of positional selectivity. Previously reported alkylations showing a high degree of meta substitution, therefore, must have been affected by thermodynamically controlled rearrangement processes, including intramol. alkyl and H shifts in the arenium ion intermediates of the alkylation reactions. These are to be differentiated from possible subsequent product isomerizations. Under predominantly kinetic conditions anisole as well as toluene is substantially ortho-para directing in alkylations, as in other electrophilic aromatic substitutions.
Journal of the American Chemical Society published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Recommanded Product: 2-Isopropylanisole.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem