Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-02-26
1976-08-17
Milestone, Norma S.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2603459, 260642R, 260678, 260683R, 260348R, C07D30112, C07C 1122, C07C 516
Patent
active
039754090
ABSTRACT:
The sexual attractant of the gypsy moth, cis-7,8-epoxy-2-methyloctadecane, is prepared by reacting isoheptyl bromide with an organometallic compound of dodecine-(1) in the presence of an anhydrous polar organic diluent at a temperature of about 20.degree. to 150.degree.C to produce 2-methyloctadecine-(7),hydrogenating the 2-methyloctadecine-(7) in the presence of a palladium catalyst and at a temperature of about -10.degree. to +60.degree.C in a diluent to produce 2-methyloctadecene-7-cis and epoxidizing the 2-methyloctadecene-7-cis to produce cis-7,8-epoxy-2-methyloctadecane. The organometallic compound of dodecine-1 is prepared by reaction of dodecine-1 with lithium, sodium or potassium amide freshly prepared in liquid ammonia or a solution of alkyl-lithium. The isoheptyl bromide is prepared by converting propargyl alcohol into 3-tetrahydropyranyloxypropine-(1), reacting the 3-tetrahydropyranyloxypropine-(1) with metallic lithium, sodium or potassium in liquid ammonia or with a Grignard compound to produce the corresponding organometallic compound, reacting the organometallic compound in an inert anhydrous organic solvent at a temperature of about -20.degree. to +50.degree.C with an approximately equimolar amount of freshly distilled isobutyraldehyde to produce 1-tetrahydropyranyloxy-5-methylhexin-(3)-ol-(4), hydrogenating the 1-tetrahydropyranyloxy-5-methylhexin-(3)-ol-(4) with excess Pd/carbon catalyst at a temperature of about 0.degree. to 100.degree.C to produce isoheptanol and converting the isoheptanol to isoheptyl bromide.
REFERENCES:
patent: 3453362 (1969-07-01), Cruickshank
B. A. Bierl et al., Science, vol. 170, Oct. 2, 1970, pp. 87-89.
B. B. Elsner et al., Jour. Chem. Soc. (London) (1953) pp. 3156-3160. 2-methyloctadecine-(7), hydrogenating
Bayer Aktiengesellschaft
Milestone Norma S.
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