Ultrasound-assisted self-metathesis reactions of monounsaturated fatty acids | OCL

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Table 4

Results of self-metathesis reactions of elaidic acid (4) and erucic acid (5)^[a].

Entry	Starting	Solvent	Conv	Diacid (%)^[d]	Alkene (%)^[d]
Entry	material	Solvent	(%)^[c]	Diacid (%)^[d]	Alkene (%)^[d]

1	Oleic acid (1)	DCM^[b]	94	1,18-Octadec-	Octadec-9-
				9-enedioic	ene (3, 65)
				acid (2, 75)
2	Oleic acid (1)	1-Butanol	90	1,18-Octadec-	Octadec-9-
				9-enedioic	ene (3, 59)
				acid (2, 67)
3	Elaidic acid (4)	DCM	60	1,18-Octadec-	Octadec-9-
				9-enedioic	ene (3, 58)
				acid (2, 48)
4	Elaidic acid (4)	1-Butanol	55	1,18-Octadec-	Octadec-9-
				9-enedioic	ene (3, 53)
				acid (2, 45)
5	Erucic acid (5)	DCM	94	1,26-Hexacos-	Octadec-9-
				13-enedioic	ene (3, 55)
				acid (6, 72)
6	Erucic acid (5)	1-Butanol	93	1,26-Hexacos-	Octadec-9-
				13-enedioic	ene (3, 58)
				acid (6, 58)

^[a]

Reaction conditions: Fatty acid (20 mmol), C1 (0.1 mol%), solvent, ultrasound, 1 h.

^[b]

DCM: dichloromethane.

^[c]

Substrate conversion was determined by GC, with pentadecanoic acid as the internal reference.

^[d]

Yields were determined after purification by flash chromatography on silica gel.

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