dec-9-enoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound G was prepared from 9-decen-1-ol and 9-decenoic acid following the general procedure already discussed and shown in FIG. 12. Pure compound G was a colorless oil by column chromatography with Ethyl acetate/Hexane=1:50.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound E was prepared from Oleyl alcohol and 9-decenoic acid following the general procedure previously discussed and shown in FIG. 10. Pure compound E was a colorless oil obtained by column chromatography with Ethyl acetate/Hexane=1:40.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethenolysis of the nitrile of oleic acid is carried out at 60° C. under atmospheric pressure in the presence of a ruthenium-based catalyst, [RuCl2(═CHPh)(IMesH2)(PCy3)], using an excess of ethylene, to give 9-decenoic acid, CH2═CH—(CH2)7—COOH. The yields are determined by chromatographic analysis. At the end of the reaction, 6 hours, the C10 α-olefin is separated by vacuum distillation, to give the 9-decenoic nitrile CH2═CH—(CH2)7—CN. The yields are determined by chromatographic analysis. It is possible to measure a yield of 55%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preferably, the cross metathesis reaction with acrylonitrile is carried out with a compound chosen from 9-decenoic acid or methyl 9-decenoate, resulting from the ethenolysis of oleic acid or methyl oleate, 10-undecenoic acid or methyl 10-undecenoate, resulting from the cracking of ricinoleic acid or methyl ricinoleate, oleic acid or methyl oleate, 9-octadecenedioic acid or methyl 9-octadecenedioate, resulting from the homometathesis or fermentation of oleic acid, erucic acid and methyl erucate, or 12-tridecenoic acid or methyl 12-tridecenoate, resulting from lesquerolic acid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound G was prepared from 9-decen-1-ol and 9-decenoic acid following the general procedure already discussed and shown in FIG. 12. Pure compound G was a colorless oil by column chromatography with Ethyl acetate/Hexane=1:50.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound E was prepared from Oleyl alcohol and 9-decenoic acid following the general procedure previously discussed and shown in FIG. 10. Pure compound E was a colorless oil obtained by column chromatography with Ethyl acetate/Hexane=1:40.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethenolysis of the nitrile of oleic acid is carried out at 60° C. under atmospheric pressure in the presence of a ruthenium-based catalyst, [RuCl2(═CHPh)(IMesH2)(PCy3)], using an excess of ethylene, to give 9-decenoic acid, CH2═CH—(CH2)7—COOH. The yields are determined by chromatographic analysis. At the end of the reaction, 6 hours, the C10 α-olefin is separated by vacuum distillation, to give the 9-decenoic nitrile CH2═CH—(CH2)7—CN. The yields are determined by chromatographic analysis. It is possible to measure a yield of 55%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethenolysis of the nitrile of oleic acid is carried out at 60° C. under atmospheric pressure in the presence of a ruthenium-based catalyst, [RuCl2(═CHPh)(IMesH2)(PCy3)], using an excess of ethylene, to give 9-decenoic acid, CH2═CH—(CH2)7—COOH. The yields are determined by chromatographic analysis. At the end of the reaction, 6 hours, the C10 α-olefin is separated by vacuum distillation, to give the 9-decenoic nitrile CH2═CH—(CH2)7—CN. The yields are determined by chromatographic analysis. It is possible to measure a yield of 55%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the aforementioned procedure, diene was prepared from dec-9-enoic acid and but-3-en-1-ol. The resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether) to afford the desired product as a colorless oil. IR (neat): 3077 (m), 2927 (s), 2855 (s), 1737 (s), 1641 (m), 1458 (m), 1418 (m), 1353 (m), 1243 (s), 1170 (s), 1115 (m), 992 (s), 912 (s), 725 (m), 635 (m); 1H NMR (400 MHz, CDCl3): δ 5.86-5.74 (2H, m), 5.14-4.91 (4H, m), 4.12 (2H, t, J=6.8 Hz), 2.38 (2H, ddt, J=13.6, 6.8, 1.4 Hz), 2.29 (2H, t, J=7.6 Hz), 2.06-2.01 (2H, m), 1.63-1.59 (2H, m), 1.39-1.26 (8H, m); 13C NMR (100 MHz, CDCl3): δ 174.0, 139.3, 134.2, 117.3, 114.3, 63.4, 34.5, 33.9, 33.3, 29.2, 29.2, 29.1, 29.0, 25.1; HRMS (ESI+) [M+H]+ calcd for C14H25O2: 225.1855. found: 225.1855. The resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the aforementioned procedure, diene was prepared from dec-9-enoic acid and but-3-en-1-ol. The resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether) to afford the desired product as a colorless oil. IR (neat): 3077 (m), 2927 (s), 2855 (s), 1737 (s), 1641 (m), 1458 (m), 1418 (m), 1353 (m), 1243 (s), 1170 (s), 1115 (m), 992 (s), 912 (s), 725 (m), 635 (m); 1H NMR (400 MHz, CDCl3): δ 5.86-5.74 (2H, m), 5.14-4.91 (4H, m), 4.12 (2H, t, J=6.8 Hz), 2.38 (2H, ddt, J=13.6, 6.8, 1.4 Hz), 2.29 (2H, t, J=7.6 Hz), 2.06-2.01 (2H, m), 1.63-1.59 (2H, m), 1.39-1.26 (8H, m); 13C NMR (100 MHz, CDCl3): δ 174.0, 139.3, 134.2, 117.3, 114.3, 63.4, 34.5, 33.9, 33.3, 29.2, 29.2, 29.1, 29.0, 25.1; HRMS (ESI+) [M+H]+ calcd for C14H25O2: 225.1855. found: 225.1855. The resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether)

Conditions: temp:0.00; pressure:0.00; stir: