Hydrochloric Acid → 7-Methoxy-2-methylbenzofuran

Temperature

217.5 °C

To a well stirred solution of 1-methoxy-2-(2-propenyloxy)benzene (from step 1) (13.0 g, 80.24 mmol) in N,N-diethyl aniline (130 mL) was added cesium fluoride (15.85 g, 104 mmol) and the mixture was heated to 215-220° C. for 4-5 hours. Reaction mixture was cooled to room temperature and 10% aqueous HCl solution (1.0 lit) was added followed by addition of ethyl acetate (300 mL). The mixture was the filtered through Celite bed. The organic layer was separated and washed with water (2×100 mL) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave crude product (11.0 g) as dark brown oil. It was then purified through silica gel column using petroleum ether: ethyl acetate (9:1) as an eluent to afford the product as pale yellow oil (4.6 g).

1. customReaction mixture
2. temperaturewas cooled to room temperature
3. filtrationfiltered through Celite bed
4. customThe organic layer was separated
5. washwashed with water (2×100 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. customRemoval of solvent under vacuo
8. customgave crude product (11.0 g) as dark brown oil
9. customIt was then purified through silica gel column

ORD record

ord-76ef8db85d0b47a4909a421b6c08dc7c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943634B2