Metathesis syntheses of pheromones or their components

A method for synthesizing a metathesis product, comprising:

• selecting a first terminal olefin;
• selecting a second terminal olefin;
• cross-metathesizing the first terminal olefin and the second terminal olefin in the presence of a metathesis catalyst selected from Class I-IV metathesis catalysts to form the metathesis product and a side product;
• and
• applying conditions of sufficiently high temperature and/or sufficiently low pressure such that the side product evaporates out of the reaction chamber.

A method for synthesizing olefinic alcohols, acetates, aldehydes, carboxylic acids or derivatives thereof in a reaction chamber, comprising:

• self-metathesizing a first alpha olefin of form R—(CH═CH)k(CH2)n(CHX)g(CH2)m—H, where X is selected from a hydrogen, an alcohol, an acetate, a carboxylate ester, a carboxylic acid, an aldehyde, a halide, or a tosylate, mesylate, or derivatives thereof, and n and m are each selected from zero and an integer less than or equal to 20, in the presence of a first metathesis catalyst to produce a first product of form (CH═CH)k[(CH2)n(CHX)g(CH2)m—H]2 and a first side product of form RHC═CHR, where R is selected from H, CH2 or (CH2)n(CHX)g(CH2)m—H;
• and
• cross-metathesizing the first product with a second alpha olefin of form QCH(CH2)rW, where Q is selected from CH2 or CH(CH2)rW, r is selected from zero and an integer less than or equal to 20, and W is selected from an alcohol, acetate, carboxylate ester, carboxylic acid, an aldehyde, a halide, hydrogen, or derivatives thereof in the presence of a second metathesis catalyst to form a second product of form H(CH2)m(CHX)g(CH2)n(CH═CH)p(CH2)rW or derivatives thereof, where p is less than or equal to the sum of m and n, and a second side product in the form of CH2Z, where Z is selected from CH2 or CH(CH2)n(CHX)g(CH2)mCH3 under conditions of sufficiently high temperature and/or sufficiently low pressure such that the second side product evaporates out of the reaction chamber.

A method of synthesizing an omega-haloalkyl product, comprising:

• selecting an alpha-omega-diacetoxy alkene;
• selecting an alpha-omega-dihalide;
• and
• cross-metathesizing the alpha-omega-diacetoxy alkene with the alpha-omega-dihalide in the presence of a metathesis catalyst to produce an omega-haloalkenyl acetate.

A method of removing a metathesis catalyst from a reaction mixture including a metathesis product or reactant, comprising:

• introducing an amount of a water soluble phosphine or a water soluble phosphite into the reaction mixture wherein the metathesis catalyst is selected Class I-IV metathesis catalysts;
• mixing the reaction mixture to create an aqueous phase;
• and
• removing the aqueous phase containing the metathesis catalyst.

A method for synthesizing 5-decenyl acetate comprising the steps of:

• self-metathesizing 1-hexene in the presence of catalyst 823 to form a mixture of 5-decene and ethylene;
• removing the ethylene from the mixture;
• cross-metathesizing the 5-decene with a protected hexene having a formula 5-hexene-1-R, where R includes an alcohol, acetate, ether, halide, or ester, in the presence of catalyst 823 to form 1-hexene and 5-decenyl acetate having a trans:cis ratio of greater than 80:20;
• performing the cross-metathesizing step under vacuum to remove the 1-hexene as it is formed;
• and
• producing a gross yield of 5-decenyl acetate that is greater than 30 percent.