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Table 2 Fe3+-cit/Na2S2O8 catalyzed methyl linoleate hydroxylation to a mixture of conjugated hydroxy-octadecanoate methyl ester in different solvents

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

Entry Solvent (v/v) Conv.% Yield of CHLM%
1a MeCN/H2O (4/1) 100 95.3 ± 3.2(88.7 ± 3.3)
2 MeCN alone 100 21.9 ± 4.1
3 H2O alone 98.2 ± 1.8 24.8 ± 2.5
4 MeCN/H2O (2/1) 93.7 ± 3.4 64.3 ± 4.2
5 MeCN/H2O (1/1)  > 99 48.7 ± 2.4
6 THF/ H2O 45.6 ND
7 MeOH 60.4 ND
8 DMSO 45.5 ND
9 DMF 69.7 ND
  1. 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 (13.1 mg) and Na2S2O8 (6 equiv.). Reaction mixture was stirred 24 h at 80 °C under O2 balloon. Yield determined by HPLC with internal standard
  2. aIsolated and, determined yield by 1H NMR analysis with internal standard, N.D. = Not detected