Iodine → 2-(2-Ethoxyphenyl)ethanol

Temperatur

0 °C

Into a 250-mL 3-necked round-bottom flask, maintained with an inert atmosphere of nitrogen, was placed Mg (1.0 g, 41.67 mmol, 2.09 equiv) and I2 (10 mg). Then a solution of 1-bromo-2-ethoxybenzene (4.0 g, 19.89 mmol, 1.00 equiv) in 25 mL THF was added dropwise and the resulting mixture was heated to reflux for 0.5 hr. After the reaction was complete, the resulting mixture was cooled to 0° C. and then oxirane (50 mL) was added in one portion. The reaction mixture was stirred overnight at room temperature. The reaction was then quenched by the addition of 50 mL of NH4Cl (aq.) and extracted with 3×50 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). Purification afforded 2.14 g (65%) of 2-(2-ethoxyphenyl)ethan-1-ol as a yellow oil.

1. temperatureInto a 250-mL 3-necked round-bottom flask, maintained with an inert atmosphere of nitrogen
2. temperaturethe resulting mixture was heated
3. temperatureto reflux for 0.5 hr
4. customThe reaction was then quenched by the addition of 50 mL of NH4Cl (aq.)
5. extractionextracted with 3×50 mL of ethyl acetate
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customPurification

ORD-Eintrag

ord-04e2eb17b10849ed8ef3f4e8d2fcc490

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08969557B2