2-Methoxybenzaldehyde → 2-(2-Methoxyphenyl)oxirane

Temperature

40 °C

Into a 1000-mL 3-necked round-bottom flask was placed DMSO (400 mL) and sodium hydride (7 g, 175.00 mmol, 1.19 equiv, 60%). This was followed by the addition of S,S-dimethylmethanesulfinyl iodide (38 g, 172.67 mmol, 1.18 equiv). The mixture was stirred for 1 h at 40° C. To this was added a solution of 2-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 equiv) in DMSO (100 mL) dropwise with stirring at 15° C. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 400 mL of NH4Cl (aq.). The resulting solution was extracted with 1000 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1000 mL of H2O. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. Purification afforded 14 g (63%) of 2-(2-methoxyphenyl)oxirane as a yellow oil.

1. customInto a 1000-mL 3-necked round-bottom flask was placed
2. stirringwith stirring at 15° C
3. stirringThe resulting solution was stirred for 1 h at room temperature
4. customThe reaction was then quenched by the addition of 400 mL of NH4Cl (aq.)
5. extractionThe resulting solution was extracted with 1000 mL of ethyl acetate
6. washThe resulting mixture was washed with 1000 mL of H2O
7. dry with materialThe mixture was dried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. customPurification

ORD record

ord-99efad504ed247058a126dca25dd79b7

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2