Dimethylformamide → 3-(Bicyclo[2.2.1]hept-2-yloxy)-4-methoxybenzaldehyde

Temperature

80 °C

Isovanillin (50 g, 0.328 mol) is placed in a 1 liter round bottom flask which is equipped with a stir bar and reflux condenser and is charged with 500 ml of dimethylformamide, Potassium carbonate (45.3 , 0.328 mol) is added to the reaction mixture which is heated to 80° C. At this temperature exo-2-bromonorbornane (12.57 g, 0.072 mol, 0.219 equivalents) is added and the reaction mixture is heated to 120° C. for 48 hours. The reaction is then cooled to room temperature and poured into 300 ml of water. The aqueous layer is extracted with ethyl ether (3×100 ml). The ethereal layer is washed with 1N sodium hydroxide solution. (4×100 ml), water (3×100) ml) and saturated sodium chloride solution (3×100 ml). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 15.47 g of a green/brown oil. The crude product is purified with flash chromatography using a gradient eluent system of ethyl acetate/hexane [10% ethyl acetate/hexane →20% ethyl acetate/hexane] to yield 7.76 g (14.4%) of the aldehyde as a white solid. MP: 75.5° C.-79.5° C.

1. customwhich is equipped with a stir bar
2. temperaturereflux condenser
3. additionis added to the reaction mixture which
4. temperaturethe reaction mixture is heated to 120° C. for 48 hours
5. temperatureThe reaction is then cooled to room temperature
6. extractionThe aqueous layer is extracted with ethyl ether (3×100 ml)
7. washThe ethereal layer is washed with 1N sodium hydroxide solution
8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-f3c2d93607434f28b0139470e71c5d76

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05196426