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

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Table 3

Solvent-screening results for self-metathesis reactions of oleic acid (1)^[a].


Entry	Solvent	Conv.	2 (%)^[e]	2, E/Z^[e]	3 (%)^[e]
Entry	Solvent	(%)^[d]	2 (%)^[e]	2, E/Z^[e]	3 (%)^[e]

1	DMC^[b]	91	57	4/1	58
2	Ethanol	68	24	3/1	23
3	1-Propanol	74	48	3/1	47
4	1-Butanol	91	67	4/1	59
5	2-Butanol	90	66	4/1	65
6	Iso-butanol	90	60	4/1	63
7	Iso-hexane	89	61	4/1	61
8	Chloroform	90	50	4/1	57
9	DCM^[c]	94	75	11/1	65

^[a]

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

^[b]

DMC: dimethyl carbonate. Reaction time: 5 h.

^[c]

DCM: dichloromethane.

^[d]

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

^[e]

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

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