Process for preparing 2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane

19:

• A process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I)
• any one of its individual enantiomers or any non-racemic mixture thereof comprising the steps of
• (a) deprotonating (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II)
• any one of its individual enantiomers or any non-racemic mixture thereof
• in the presence of at least one base of the formula [Mm+]n [An−]m (III) wherein Mm+ represents a m-valent metal cation wherein m is an integer of 1 or 2, and An− represents a n-valent anion wherein n is an integer of 1 or 2, said base being capable of forming a solvent S1 selected from water, a C1-C4 alkyl alcohol or any combination thereof under the reaction conditions, to form a metal alkoxide or metal alkoxide solvate of the formula (IV)
• any one of its individual enantiomers or any non-racemic mixture thereof wherein Mm+, m and the solvent S1 have the same meaning as defined for the base of formula (III), and x denotes a number from 0 to 10, and
• (b) reacting the metal alkoxide or metal alkoxide solvate of the formula (IV), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (V)
• wherein X is a leaving group,
• wherein the steps (a) and (b) are conducted in the presence of at least one inert organic solvent S2 and comprise a further step of (c) simultaneously removing the solvent S1 from the reaction mixture.

36:

• A method for preventing or reducing the formation of deposits on the interior of a reactor in which the preparation of (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I)
• any one of its individual enantiomers or any non-racemic mixture thereof is conducted by benzylating (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II)
• any one of its individual enantiomers or any non-racemic mixture thereof with a 2-methylbenzyl compound of the formula (V)
• wherein X is a leaving group, said method comprising the steps of
• (a) deprotonating (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof in the presence of at least one base of the formula [Mm+]n [An−]m (III) wherein Mm+ represents a m-valent metal cation wherein m is an integer of 1 or 2, and An− represents a n-valent anion wherein n is an integer of 1 or 2, said base being capable of forming a solvent S1 selected from water, a C1-C4 alkyl alcohol or any combination thereof under the reaction conditions, to form a metal alkoxide or metal alkoxide solvate of the formula (IV)
• any one of its individual enantiomers or any non-racemic mixture thereof wherein Mm+, m and the solvent S1 have the same meaning as defined for the base of formula (III), and x denotes a number from 0 to 10, and
• (b) reacting the metal alkoxide or metal alkoxide solvate of the formula (IV), any of its individual enantiomers or any non-racemic mixture thereof with the 2-Methylbenzyl compound of the formula (V)
• wherein the steps (a) and (b) are conducted in the presence of at least one inert organic solvent S2 and comprise a further step of (c) simultaneously removing the solvent S1 from the reaction mixture.