Process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate and intermediates thereof

A process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3):

• wherein Ac represents an acetyl group,
• the process comprising steps of:
• subjecting a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1):
• wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group,
• to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2):
• and
• acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

A process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3):

• wherein Ac represents an acetyl group,
• the process comprising steps of:
• subjecting a nucleophilic reagent, 2-isopropenyl-5-hexenyl compound, of the following general formula (5):
• wherein M2 represents Li, MgZ2, ZnZ2, Cu, CuZ2, or CuLiZ2, wherein Z2 represents a halogen atom or a 2-isopropenyl-5-hexenyl group,
• to a coupling reaction with a 1,3-dihalo-2-methylpropane compound of the following general formula (6):
• wherein X1 represents, independently of each other, a halogen atom,
• to form a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4):
• wherein X1 represents a halogen atom;
• preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1):
• wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group,
• from the 5-isopropenyl-2-methyl-8-nonenyl halide compound (4);
• subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2):
• and
• acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).