(6z)-6-tridecenyl metal compound, process for preparing the same, and process for preparing (7z)-7-tetradecenal

A process for preparing a (6Z)-6-tridecenyl metal compound of the following general formula (1):

• wherein M1 represents Li or MgZ1, and Z1 represents a halogen atom or a (6Z)-6-tridecenyl group, the process comprising steps of:
• preparing a (3Z)-3-decenyl metal compound of the following general formula (3):
• wherein M2 represents Li or MgZ2, and Z2 represents a halogen atom or a (3Z)-3-decenyl group, from a 1-halo-(3Z)-3-decene compound of the following general formula (2):
• wherein X1 represents a halogen atom;
• subjecting the (3Z)-3-decenyl metal compound (3) to a coupling reaction with a 1,3-dihalopropane compound of the following general formula (4):
• wherein X2 and X3 represent, independently of each other, a halogen atom,
• to form a 1-halo-(6Z)-6-tridecene compound of the following general formula (5):
• wherein X4 represents a halogen atom;
• and
• preparing the aforesaid (6Z)-6-tridecenyl metal compound (1) from the 1-halo-(6Z)-6-tridecene compound (5).

A process for preparing (7Z)-7-tetradecenal of the following formula (8):

• the process comprising steps of:
• subjecting a (6Z)-6-tridecenyl metal compound of the following general formula (1):
• wherein M1 represents Li or MgZ1, and Z1 represents a halogen atom or a (6Z)-6-tridecenyl group, to a nucleophilic substitution reaction with an orthoformate ester compound of the following general formula (6):
• wherein R1, R2, and R3 represent, independently of each other, an alkyl group having 1 to 6 carbon atoms,
• to form a 1,1-dialkoxy-(7Z)-7-tetradecene compound of the following general formula (7):
• wherein R4 and R5 represent, independently of each other, an alkyl group having 1 to 6 carbon atoms;
• and
• subjecting the 1,1-dialkoxy-(7Z)-7-tetradecene compound (7) to a hydrolysis reaction to form the aforesaid (7Z)-7-tetradecenal (8).