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

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.

1. stirringAfter stirring at RT for 1 hr
2. customthe reaction is quenched with water (5 ml)
3. extractionextracted with EtOAc (2×50 ml)
4. washThe combined organic extracts are washed with Na2CO3 (2M, 50 ml)
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customThe resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane

ORD record

ord-a0e6c7db45f4437e87a00d7d1a3e697f

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994203B2