Process for preparing (Z)-7-tetradecen-2-one
The present invention relates to a process for preparing (Z)-7-tetradecen-2-one of the following formula (5), the process comprising the steps of converting a (Z)-1-halo-4-undecene compound (1) of the following general formula (1), wherein X 1 represents a halogen atom, into a nucleophilic reagent, (Z)-4-undecenyl compound, of the following general formula (2), wherein M 1 represents Li or MgZ 1 , and Z 1 represents a halogen atom or a (4Z)-4-undecenyl group, subjecting the nucleophilic reagent, (Z)-4-undecenyl compound (2), to an addition reaction with propylene oxide of the following formula (3) to obtain (Z)-7-tetradecen-2-ol of the following formula (4) and oxidizing (Z)-7-tetradecen-2-ol (4) thus obtained to form (Z)-7-tetradecen-2-one (5).
1 . A process for preparing (Z)-7-tetradecen-2-one of the following formula (5):
the process comprising the steps of:
converting a (Z)-1-halo-4-undecene compound (1) of the following general formula (1):
wherein X 1 represents a halogen atom,
into a nucleophilic reagent, (Z)-4-undecenyl compound, of the following general formula (2):
wherein M 1 represents Li or MgZ 1 , and Z 1 represents a halogen atom or a (4Z)-4-undecenyl group,
subjecting the nucleophilic reagent, (Z)-4-undecenyl compound (2), to an addition reaction with propylene oxide of the following formula (3):
to obtain (Z)-7-tetradecen-2-ol of the following formula (4):
and oxidizing (Z)-7-tetradecen-2-ol (4) thus obtained to form (Z)-7-tetradecen-2-one (5).
2 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 1 , wherein the oxidization is carried out by an Oppenauer oxidation.
3 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 1 , the process further comprising:
esterifying the (Z)-7-tetradecen-2-ol (4) remaining after the aforesaid step of obtaining (Z)-7-tetradecen-2-one (5).
4 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 3 , the process further comprising the step of:
purifying (Z)-7-tetradecen-2-one (5) from a reaction mixture of (Z)-7-tetradecen-2-one (5) and an esterified product of (Z)-7-tetradecen-2-ol (4) after the step of esterification.
5 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 1 , the process further comprising the step of:
subjecting a 1-halo-4-undecyne compound of the following general formula (6):
wherein X 1 represents a halogen atom,
to a reduction reaction to obtain the (Z)-1-halo-4-undecene compound (1).
6 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 5 , the process further comprising the step of:
subjecting a nucleophilic reagent, hexyl compound, of the following general formula (7):
wherein M 2 represents Li or MgZ 2 , and Z 2 represents a halogen atom or a hexyl group,
to a coupling reaction with a 1,5-dihalo-1-pentyne compound of the following general formula (8):
wherein X 1 and X 2 represent, independently of each other, a halogen atom,
to form 1-halo-4-undecyne (6).
7 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 2 , the process further comprising:
esterifying the (Z)-7-tetradecen-2-ol (4) remaining after the aforesaid step of obtaining (Z)-7-tetradecen-2-one (5).
8 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 7 , the process further comprising the step of:
purifying (Z)-7-tetradecen-2-one (5) from a reaction mixture of (Z)-7-tetradecen-2-one (5) and an esterified product of (Z)-7-tetradecen-2-ol (4) after the step of esterification.
9 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 2 , the process further comprising the step of:
subjecting a 1-halo-4-undecyne compound of the following general formula (6):
wherein X 1 represents a halogen atom,
to a reduction reaction to obtain the (Z)-1-halo-4-undecene compound (1).
10 . The process for preparing (Z)-7-tetradecen-2-one (5) according to claim 9 , the process further comprising the step of:
subjecting a nucleophilic reagent, hexyl compound, of the following general formula (7):
wherein M 2 represents Li or MgZ 2 , and Z 2 represents a halogen atom or a hexyl group,
to a coupling reaction with a 1,5-dihalo-1-pentyne compound of the following general formula (8):
wherein X 1 and X 2 represent, independently of each other, a halogen atom,
to form 1-halo-4-undecyne (6).