A method of making a 3-alkylcycloalkanol of formula 2: where R1 represents
a methyl or ethyl group, R2 represents hydrogen, R3 represents
an ethyl, propyl, butyl, isobutyl or isoamyl group, R4 represents hydrogen
and R5 represents hydrogen, or a methyl, ethyl, propyl, isobutyl or
isoamyl group comprises the following steps: (1) carrying out an electrophilic
substitution reaction of an alkyl group or precursor thereof, on an ortho-substituted
alkylbenzene compound of formula 3: where R6 represents hydrogen, or
a methyl or ethyl group; (2) hydrogenating the reaction product of step (1); (3)
performing an elimination reaction on one or more reaction products of step (2)
to produce one or more alkene products; and (4) hydrating the one or more alkene
products of step (3) to provide a 3-alkylcycloalkanol of formula 2. The electrophilic
substitution reaction of step (1) may be a Friedel-Crafts acylation, e.g. using
an isopropyl ketone precursor, or a Friedel-Crafts alkylation, e.g. using an isobutyl
group. The 3-alkylcycloalkanols, especially 3-(2-methylpropyl)-1-methylcyclohexanol,
are useful fragrance materials and find use in perfumes and perfumed products.
