Epichlorohydrin → 2-[(4-Ethoxyphenoxy)methyl]oxirane

4-Ethoxyphenol (0.25 g, 1.81 mmol), anhydrous potassium carbonate (0.50 g, 3.62 mmol) and epichlorohydrin (0.57 ml, 7.24 mmol) were added to acetone (4.52 ml) and the resulting heterogeneous solution was refluxed for 16 hrs. The mixture was cooled to room temperature, filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The resulting oil was dissolved in toluene (20 mL), washed sequentially with water (15 mL), 5% aqueous NaOH (20 mL) and water again (20 mL). The organic layer was dried with MgSO4 and concentrated under reduced pressure to yield 0.292 g (83%) of 2-((4-ethoxyphenoxy)methyl)oxirane as a white solid (mp=41° C.). 1H NMR (400 MHz, CDCl3) δ 6.91-6.77 (m, 4H), 4.17 (dd, J=11.0, 3.2, 1H), 3.98 (q, J=7.0, 2H), 3.91 (dd, J=11.0, 5.6, 1H), 3.34 (m, 1H), 2.90 (dd, J=4.9, 4.1, 1H), 2.75 (dd, J=5.0, 2.7, 1H), 1.39 (t, J=6.98, 3H). 13C NMR (75 MHz, CDCl3) δ 153.72, 152.78, 115.90, 115.90, 115.59, 115.59, 69.71, 64.18, 50.49, 44.98, 15.15. HRMS (m/z): [MNa]+ calc. for C11H14O3Na+, 217.08. found 217.0826.

1. temperaturethe resulting heterogeneous solution was refluxed for 16 hrs
2. filtrationfiltered through a pad of celite
3. concentrationthe filtrate was concentrated under reduced pressure
4. dissolutionThe resulting oil was dissolved in toluene (20 mL)
5. washwashed sequentially with water (15 mL), 5% aqueous NaOH (20 mL) and water again (20 mL)
6. dry with materialThe organic layer was dried with MgSO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-33371cca0035466abdd5d450be84e86b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642614B2