Efficient and selective catalytic hydroxylation of unsaturated plant oils: a novel method for producing anti-pathogens

Table 1 The hydroxylation of methyl linoleate (ML) in presence of the iron catalyst with different sulfate metal ions

Entry	Catalyst	Ligands	Conv.%	Yield of CHLM%
1	FeCl₃	Na₂S₂O₈	52.2	N.D
2	FeCl₃·6H₂O	Na₂S₂O₈	67.3	18.6 ± 1.4
3	FeCl₂·4H₂O	Na₂S₂O₈	45.5	21.3 ± 5.4
4	Fe₂(SO₄)₃	Na₂S₂O₈	58.1	13.5 ± 4.6
5	FePc	Na₂S₂O₈	> 90	N.D
6^a	Fe³⁺-cit·H₂O	Na₂S₂O₈	100	95.3 ± 3.2(88.7 ± 3.3)
7	Fe³⁺-cit·H₂O	Na₂S₂O₃·5H₂O	87.9	81.7 ± 3.5
8	Fe³⁺-cit·H₂O	NaO₃V	82.0	14.2 ± 4.2
9^b	Fe³⁺-cit·H₂O	Na₂SeO₃	100	18.3 ± 5.2
10	Fe³⁺-cit·H₂O	NaCNBH₃	100	21.3 ± 2.1
11^c	Fe³⁺cit· H₂O	Na₂S₂O₈	100	33.4 ± 2.5
12^d	Fe³⁺-cit·H₂O	Na₂S₂O₈	97.2 ± 1.3	73.2 ± 5.2
13	Fe³⁺-cit·H₂O	–	19.7 ± 2.1	11.5 ± 1.5
14	–	Na₂S₂O₈	100	38.2 ± 4.1
15	Fe³⁺-cit·H₂O	Sc(OTf)₃	54	N.D
16	Fe³⁺-cit·H₂O	H₂O₂	80.2 ± 5.5	59.4 ± 5.2

Condition: in mixture solvent MeCN/H₂O (v/v, 4 mL/1 mL), the 1.0 mmol (316.6 µL), of methyl linoleate was added to the solution containing Fe(III) citrate -monohydrate 0.05 mmol and Na₂S₂O₈ (6 equiv.). Reaction mixture was stirred 24 h at 80 °C under O₂ balloon. Yield determined by HPLC with internal standard
^aIsolated and, determined yield by ¹H NMR analysis with internal standard, N.D. = Not detected
^bReaction at 50 °C
^cReaction under Argon
^dReaction under air

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