Production of 3-alkylcycloalkanols

Details Production of 3-alkylcycloalkanols Production of 3-alkylcycloalkanols

2005-05-31

2005-05-31

Shippen, Michael L. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S822000

Reexamination Certificate

active

06900359

ABSTRACT:
A method of making a 3-alkylcycloalkanol of formula 2: where R1represents a methyl or ethyl group, R2represents hydrogen, R3represents an ethyl, propyl, butyl, isobutyl or isoamyl group, R4represents hydrogen and R5represents 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 R6represents 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.

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