反应详情

A dry 3-neck, 1 L flask equipped with a N2 inlet and dropping funnel is charged with dry THF (200 mL) and LiAlH4 (1.90 g, 0.050 mole). To the stiffed mixture is added via the dropping funnel a hot solution of naphthalene-1,4-dicarboxylic acid (4.32 g, 0.020 mole) in THF (200 mL) over a period of about 1 hour. The resulting mixture is stirred without heating for 90 minutes and then is heated to reflux temperature. After 2 hours, additional LiAlH4 (40 mL of a 1.15 M solution in THF) is added and refluxing continued for 90 minutes. The reaction is stirred at room temperature overnight, then is quenched carefully with THF-water (3:1), acidified to PH <4 with 2N hydrogen chloride, transferred to a separatory funnel and extracted (3 times) with ether. The combined ether extracts are washed with water (2 times), dried (sodium sulfate), filtered, and concentrated to give a white solid (3.68 g). The solid is crystallized from ethyl acetate-hexane, giving (2.68 g) as white crystals, mp 124°-126° C.

1. customA dry 3-neck, 1 L flask equipped with a N2 inlet
2. temperaturewithout heating for 90 minutes
3. temperatureis heated
4. temperatureto reflux temperature
5. temperaturerefluxing
6. waitcontinued for 90 minutes
7. stirringThe reaction is stirred at room temperature overnight
8. customis quenched carefully with THF-water (3:1)
9. customtransferred to a separatory funnel
10. extractionextracted (3 times) with ether
11. washThe combined ether extracts are washed with water (2 times)
12. dry with materialdried (sodium sulfate)
13. filtrationfiltered
14. concentrationconcentrated