Alkynyl halide compounds and alkenyl acetate compounds therefrom

A method for the preparation of 7,11-hexadecadienyl acetate having the formula

• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 CH.dbd.CH(CH.sub.2).sub.6 OCOCH.sub.3
• which comprises the steps of
• (a) reacting the Grignard reagent of a 1-halo-3-octene expressed by the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 X',
• in which X' is a halogen atom, and 1,8-dibromo-1-octyne having the formula
• Br--CH.sub.2).sub.6 C.tbd.C--Br,
• to form 1-bromohexadeca-11-en-7-yne having the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 C.tbd.C(CH.sub.2).sub.6 Br,
• (b) acetylating the 1-bromohexadeca-11-en-7-yne to form hexadeca-11-en-7-ynyl acetate having the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 C.tbd.C(CH.sub.2).sub.6 OCOCH.sub.3,
• and
• (c) partially hydrogenating the hexadeca-11-en-7-ynyl acetate in the presence of a Lindlar catalyst.

A method for the preparation of an alkenyl acetate having the formula

• R--CH.dbd.CH--CH.sub.2).sub.n OCOCH.sub.3,
• in which R is a monovalent hydrocarbon group and n is a number of 4, 5 or 6, which comprises the steps of:
• (a) reacting from 1.0 to 1.5 moles of the Grignard reagent having the formula
• RMgX',
• in which X' is a halogen atom, and 1.0 mole of an .omega.-halo-bromoalkyne compound having the formula
• X--CH.sub.2).sub.n C.tbd.C--Br,
• in a tetrahydrofuran solution at a temperature in the range from -5.degree. to +10.degree. C. in the presence of a catalytic amount of a copper halide to form an alkynyl halide compound having the formula
• R--CH.tbd.C--CH.sub.2).sub.n X,
• (b) acetylating the alkynyl halide compound by reacting it under the heating with an alkali metal acetate as diluted with acetic acid to form an alkynyl acetate compound having the formula
• R--C.tbd.C--CH.sub.2).sub.n OCOCH.sub.3,
• and
• (c) partially hydrogenating the alkynyl acetate compound in the presence of a Lindlar catalyst at a temperature of 4 to 10 atmospheres.

A method for the preparation of 7,11-hexadecadienyl acetate having the formula

• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 CH.dbd.CH(CH.sub.2).sub.6 OCOCH.sub.3
• which comprises the steps of
• (a) reacting from 1.0 to 1.5 moles of the Grignard reagent of a 1-halo-3-octene expressed by the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 X',
• in which X' is a halogen atom, and 1,8-dibromo-1-octyne having the formula
• Br--CH.sub.2).sub.6 C.tbd.C--Br,
• to form 1-bromohexadeca-11-en-7-yne having the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 C.tbd.C(CH.sub.2).sub.6 Br,
• (b) acetylating the 1-bromohexadeca-11-en-7-yne to form hexadeca-11-en-7-ynyl acetate having the formula
• CH.sub.3 (CH.sub.2).sub.3 CH.dbd.CH(CH.sub.2).sub.2 C.dbd.C(CH.sub.2).sub.6 OCOCH.sub.3,
• and
• (c) partially hydrogenating the hexadeca-11-en-7-ynyl acetate in the presence of a Lindlar catalyst.