Phenol → Allyl phenyl ether

Temperature

50 °C

To a round-bottomed flask containing a solution of phenol (30 g, 319 mmol) in acetonitrile (150 ml) at room temperature was added potassium carbonate (66 g, 478 mmol) and allyl bromide (49.8 g, 412 mmol). The mixture was heated to 50° C. and stirred for 3.5 hours. The solids were filtered out and the filtrate was concentrated to a minimum volume. The crude material was diluted with water (200 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×100 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated to afford crude allyloxybenzene as brown oil (35 g); 1H NMR (300 MHz, CDCl3): δ 7.20-7.30 (m, 2H), 6.89-6.96 (m, 3H), 5.99-6.12 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5 Hz, 1H), 4.52 (d, J=5.1 Hz, 2H).

1. filtrationThe solids were filtered out
2. concentrationthe filtrate was concentrated to a minimum volume
3. additionThe crude material was diluted with water (200 ml)
4. extractionextracted with ethyl acetate (3×100 ml)
5. washThe combined organic layers were washed with brine (2×100 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-08f88850527a44d7890a1e94c762ad12

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2