Iodine → 1-(4-Methoxy-2-methylphenyl)propan-1-one

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Reaction Steps

To a stirred suspension of samarium (598 mg, 3.97 mmol) in CH3CN is added iodine (3.0 g, 11.9 mmol, 3 eq.) and the mixture is stirred at RT for 2 hrs. 1-Methoxy-3-methylbenzene (500 μL, 3.97 mmol, 1 eq) is added followed by the dropwise addition of propionyl chloride (3472 μL, 39.7 mmol). After stirring at RT for 1 hr, the reaction is quenched with water (5 ml) and extracted with EtOAc (2×50 ml). The combined organic extracts are washed with Na2CO3 (2M, 50 ml), sat Na2S2O4 (4×50 ml), water and brine, dried over MgSO4 and concentrated under reduced pressure. The resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane to yield 1-(4-methoxy-2-methyl-phenyl)-propan-1-one as a clear oil; m/z 179.16 [M+H]+. Alternatively, intermediate C can be made by an analogous process to that for intermediate DA below.

Provenance & Evidence