aromaticcompound, any of a large class of compounds that includes benzene and compounds that resemble benzene in certain of their chemical properties.
For this reason, the bonds in the aromatic ring are less reactive than ordinary double bonds; aromaticcompounds tend to undergo ionic substitution (e.g., replacement of a hydrogen bonded to the ring with some other group) rather than addition (which would involve breaking one of the resonant bonds in the ring).
Presence of the six-membered benzene ring is not essential for aromaticcompounds; for example, furan, a heterocyclic compound that has a five-membered ring that includes an oxygen atom, has aromatic properties, as does pyridine, a heterocyclic compound whose six-membered ring includes a nitrogen atom.
In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromaticcompound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst.
However, if the alkyl-substituted aromaticcompound has, as in the case of mesitylene or isodurene, alkyl groups on both the carbon atoms adjacent to the site to be formylated, the formylation reaction thereof is extremely slow as compared with the formylation of other alkyl-substituted aromaticcompounds.
Hydrogen fluoride in excess of the starting polyalkyl-substituted aromaticcompound participates in the formation of the 1:1:1 (by mol) complex by solvating the complex, thereby enhancing the steric hindrance of the alkyl groups on both the carbon atoms adjacent to the site to be formylated to reduce the rate of formylation.
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