Methyl iodide → 1,3-Benzodioxole, 5-methoxy-

A mixture of benzo[d][1,3]dioxol-5-ol (5.000 g; 36.20 mmol), and K2CO3 (5.503 g; 39.80 mmol) in anh. acetone (100 ml) was stirred at rt, under nitrogen, for 1 h. Iodomethane (28.258 g; 199.00 mmol) was then added, and the resulting mixture was heated at reflux, under nitrogen, for 20 h. After cooling to rt, the reaction mixture was filtered over a pad of celite, and the filtrate was concentrated to dryness under reduced pressure. Et2O and water were added, and the organic layer was further washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 5-methoxybenzo[d][1,3]dioxole as a yellow oil. LC-MS (conditions A): tR=0.66 min.; no ionisation.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux, under nitrogen, for 20 h
3. temperatureAfter cooling to rt
4. filtrationthe reaction mixture was filtered over a pad of celite
5. concentrationthe filtrate was concentrated to dryness under reduced pressure
6. additionEt2O and water were added
7. washthe organic layer was further washed with brine
8. dry with materialdried over anh. MgSO4
9. filtrationfiltered
10. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-09191fdb873a41b196355e1d21cc126f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2