반응 #64754
ord-32bc6b1a7da54209a2cdb3d02c9f1c7f
반응 방정식
용매
반응 조건
후처리
- 1기타which is equipped with a stir bar
- 2온도reflux condensor
- 3온도the reaction mixture is heated to 120° C. for 48 hours
- 4온도The reaction is then cooled to room temperature
- 5추출The aqueous layer is extracted with ethyl ether (3×100 ml)
- 6세척The ethereal layer is washed with 1N sodium hydroxide solution (4×100 ml), water (3×100 ml) and saturated sodium chloride solution (3×100 ml)
- 7건조The organic layer is dried over anhydrous magnesium sulfate
- 8여과filtered
- 9농축concentrated in vacuo
실험 절차
Isovanillin (50 g, 0.328 mol) is placed in a 1 liter round bottom flask which is equipped with a stir bar and reflux condensor and is charged with 500 ml of dimethylformamide. Potassium carbonate (45.3 g, 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 by 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.