Methyl iodide → 1-Ethoxy-3-(1-methoxy-1-methylethyl)benzene

Temperature

45 °C

Sodium hydride (3.261 g, 81.54 mmol, 60% in mineral oil, Aldrich) was washed twice with hexane, and tetrahydrofuran (60 mL) was added. To this suspension was added 2-(3-ethoxy-phenyl)-propan-2-ol (4.9 g, 27.18 mmol). The mixture was stirred at 45° C. for 1.5 h until the bubbling subsided. It was cooled down to 0° C. and iodomethane (5.08 mL, 81.54 mmol, Aldrich) was added. After 4 h of stirring at room temperature, another portion of iodomethane (5.08 mL, 81.54 mmol) was added. The mixture was stirred at room temperature for 4 d then quenched at 0° C. with cold 20% solution of ammonium chloride. The product was extracted with ethyl acetate (2×1 L). The organic extracts were washed with brine and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 1-ethoxy-3-(1-methoxy-1-methyl-ethyl)-benzene (5.15 g, 97%).

1. additionwas added
2. temperatureIt was cooled down to 0° C.
3. stirringAfter 4 h of stirring at room temperature
4. stirringThe mixture was stirred at room temperature for 4 d
5. customthen quenched at 0° C. with cold 20% solution of ammonium chloride
6. extractionThe product was extracted with ethyl acetate (2×1 L)
7. washThe organic extracts were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe solids were filtered off
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-d71f84f302d44260bc41ead0e3bd6d7b

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851626B2