Hydrochloric Acid → 7-Methoxy-2-methylbenzofuran

Temperature

217.5 °C

To a well stirred solution of 1-methoxy-2-(2-propenyloxy)benzene (118.0 g, 0.728 moles) in N,N-diethyl aniline (1.0 L) was added cesium fluoride (134 g, 0.874 mmoles) 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 (3.0 lit) was added followed by addition of ethyl acetate (2.0 L). The mixture was the filtered through Celite bed. The organic layer was separated and washed with water (2×1.0 L) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave crude product (72.0 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 (2×1.0 L)
6. dry with materialdried over anhydrous sodium sulfate
7. customRemoval of solvent under vacuo
8. customgave crude product (72.0 g) as dark brown oil
9. customIt was then purified through silica gel column

ORD record

ord-c4fc5bde12514cea9c9a726da44093a9

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129401B2