Dimethyl Sulfoxide → 2-Vinylanisole

Temperature

85 °C

Under nitrogen atmosphere, in dry dimethylsulfoxide (15 mL) was suspended 1.92 g (48.0 mmol) of 60% sodium hydride washed with hexane, after stirring the suspension at 85° C. for 30 minutes, it was cooled to room temperature and then, in an ice bath, a dry dimethylsulfoxide (35 mL) solution containing 17.2 g (48.2 mmol) of methyl(triphenyl)phosphonium bromide was gradually added dropwise thereto. After stirring at room temperature for 20 minutes, 4.83 mL (40.1 mmol) of commercially available 2-methoxybenzaldehyde was added dropwise thereto, and the resulting mixture was stirred at room temperature for 1 hour and then at 65° C. for 3 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 3.29 g (24.5 mmol, Yield: 61.1%) of 1-methoxy-2-vinylbenzene.

1. washwashed with hexane
2. temperatureit was cooled to room temperature
3. additionwas gradually added dropwise
4. stirringAfter stirring at room temperature for 20 minutes
5. stirringthe resulting mixture was stirred at room temperature for 1 hour
6. waitat 65° C. for 3 hours
7. extractionextracted with ethyl acetate
8. washThe organic layer was successively washed with water and brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was removed
11. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

ORD record

ord-8898aba0b381418da12feb7edb1ed032

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964531B2