1,4-Naphthalenedicarboxylic acid → 1,4-Naphthalenedimethanol
Reaktionsgleichung
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:20](O)=[O:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](O)=[O:18])=[CH:9][CH:8]=1>C1COCC1>[C:10]1([CH2:17][OH:18])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH2:20][OH:21])=[CH:8][CH:9]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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.