1,4-Naphthalenedimethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. A dry 3-neck, 1 L flask equipped with a N2 inlet without heating for 90 minutes is heated to reflux temperature refluxing continued for 90 minutes The reaction is stirred at room temperature overnight is quenched carefully with THF-water (3:1) transferred to a separatory funnel extracted (3 times) with ether The combined ether extracts are washed with water (2 times) dried (sodium sulfate) filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. A dry 3-neck, 1 L flask equipped with a N2 inlet without heating for 90 minutes is heated to reflux temperature refluxing continued for 90 minutes The reaction is stirred at room temperature overnight is quenched carefully with THF-water (3:1) transferred to a separatory funnel extracted (3 times) with ether The combined ether extracts are washed with water (2 times) dried (sodium sulfate) filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 stirred 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 1.15M 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. A dry 3-neck, 1 L flask equipped with a N2 inlet without heating for 90 minutes is heated to reflux temperature refluxing continued for 90 minutes The reaction is stirred at room temperature overnight is quenched carefully with THF-water (3:1) transferred to a separatory funnel extracted (3 times) with ether The combined ether extracts are washed with water (2 times) dried (sodium sulfate) filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 stirred 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 1.15M 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. A dry 3-neck, 1 L flask equipped with a N2 inlet without heating for 90 minutes is heated to reflux temperature refluxing continued for 90 minutes The reaction is stirred at room temperature overnight is quenched carefully with THF-water (3:1) transferred to a separatory funnel extracted (3 times) with ether The combined ether extracts are washed with water (2 times) dried (sodium sulfate) filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The 1,4-Naphthalenedicarboxylic acid (25 g, 116 mmol) was dripped into a mixture of Lithium Aluminum Hydride (15 g, 395 mmol) in 600 mL of anhydrous THF and refluxed for two days. The mixture was cooled in an ice bath and excess LAH was decomposed by the slow addition of methanol followed by ice chips. THF was removed under vacuum and the residue was acidified with 1N HCl. The product was extracted with ethyl acetate (3×), washed with aqueous sodium bicarbonate (3×), water, brine, and dried over magnesium sulfate. 1,4-Bishydroxymethylnaphthalene (70%) was obtained as a solid after evaporation of the solvent and can be used in the subsequent oxidation step without further purification. A portion of the material was purified by column chromatography using hexane/ethyl acetate (80/20 to 75/25) for characterization purposes. refluxed for two days The mixture was cooled in an ice bath THF was removed under vacuum The product was extracted with ethyl acetate (3×) washed with aqueous sodium bicarbonate (3×), water, brine dried over magnesium sulfate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. A dry 3-neck, 1 L flask equipped with a N2 inlet without heating for 90 minutes is heated to reflux temperature refluxing continued for 90 minutes The reaction is stirred at room temperature overnight is quenched carefully with THF-water (3:1) transferred to a separatory funnel extracted (3 times) with ether The combined ether extracts are washed with water (2 times) dried (sodium sulfate) filtered concentrated