[8-(hydroxymethyl)naphthalen-1-yl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-L 3-neck flask equipped with an overhead stirrer, a condenser, and a thermocouple was charged with (8-hydroxymethyl-naphthalen-1-yl)-methanol (33.0 g, 0.175 mol), concentrated phosphoric acid (225 mL), and water (5 mL). The reaction mixture was stirred at 140° C. for 3 h, cooled to room temperature, diluted with CH2Cl2 (800 mL) and transferred to a 2-L separatory funnel. After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 and evaporated to yield 1H,3H-Benzo[de]isochromene as a solid. A 1-L 3-neck flask equipped with an overhead stirrer, a condenser cooled to room temperature transferred to a 2-L separatory funnel After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addition funnel over 1.5 h. The solution was then heated to 95° C. overnight, cooled to 15° C. and then slowly diluted with ethyl acetate (2.2 L) and H2O (2 L) followed by addition of concentrated HCl (320 mL). The resulting suspension was stirred for 30 min at room temperature, filtered, and air dried on the filter for 2 h. The resultant material was in 95% ethanol (1.2 L), stirred at 70° C. for 2 h, and filtered to yield a wet solid which was air dried overnight on the filter and then dried at 70° C. in a vacuum oven to yield (8-hydroxymethyl-naphthalen-1-yl)-methanol as a solid; A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer cooled to 15° C. The resulting suspension was stirred for 30 min at room temperature filtered air dried on the filter for 2 h stirred at 70° C. for 2 h filtered to yield a wet solid which dried overnight on the filter dried at 70° C. in a vacuum oven

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addition funnel over 1.5 h. The solution was then heated to 95° C. overnight, cooled to 15° C. and then slowly diluted with ethyl acetate (2.2 L) and H2O (2 L) followed by addition of concentrated HCl (320 mL). The resulting suspension was stirred for 30 min at room temperature, filtered, and air dried on the filter for 2 h. The resultant material was in 95% ethanol (1.2 L), stirred at 70° C. for 2 h, and filtered to yield a wet solid which was air dried overnight on the filter and then dried at 70° C. in a vacuum oven to yield (8-hydroxymethyl-naphthalen-1-yl)-methanol as a solid; A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer cooled to 15° C. The resulting suspension was stirred for 30 min at room temperature filtered air dried on the filter for 2 h stirred at 70° C. for 2 h filtered to yield a wet solid which dried overnight on the filter dried at 70° C. in a vacuum oven

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

Procedure: A mixture of naphthalene-1,8-diyldimethanol (1.15 g, 6 mmol) and CH2Cl2 (10 mL) was stirred mechanically and PBr3 (1.2 mL) added dropwise over 20 mins. During the first half of the addition the solution refluxed spontaneously. After stirring overnight at room temperature, water was added dropwise with stirring over 20 min, which again caused refluxing and evolution of much HBr. After stirring for an additional 2 h, water was added and the layers separated and the organic layer washed with water. The organic layer was evaporated in vacuum to give the crude product, which was used directly without purification (1.6 g, 84%). 1H-NMR (CDCl3): 5.30 (s, 4H), 7.44 (m, 2H), 7.62 (m, 2H), 7.87 (m, 2H). During the first half of the addition the solution refluxed spontaneously After stirring overnight at room temperature with stirring over 20 min which again caused refluxing After stirring for an additional 2 h the layers separated the organic layer washed with water The organic layer was evaporated in vacuum

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

Procedure: A mixture of naphthalene-1,8-diyldimethanol (1.15 g, 6 mmol) and CH2Cl2 (10 mL) was stirred mechanically and PBr3 (1.2 mL) added dropwise over 20 mins. During the first half of the addition the solution refluxed spontaneously. After stirring overnight at room temperature, water was added dropwise with stirring over 20 min, which again caused refluxing and evolution of much HBr. After stirring for an additional 2 h, water was added and the layers separated and the organic layer washed with water. The organic layer was evaporated in vacuum to give the crude product, which was used directly without purification (1.6 g, 84%). 1H-NMR (CDCl3): 5.30 (s, 4H), 7.44 (m, 2H), 7.62 (m, 2H), 7.87 (m, 2H). During the first half of the addition the solution refluxed spontaneously After stirring overnight at room temperature with stirring over 20 min which again caused refluxing After stirring for an additional 2 h the layers separated the organic layer washed with water The organic layer was evaporated in vacuum

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

Procedure: Benzo[de]isochromene-1,3-dione (30 g, 0.15 mol) in anhydrous THF (300 mL) was added dropwise to a solution of LAH (10 g, 0.38 mol) in anhydrous THF (200 mL). The result reaction mixture was refluxed for 3 h, then allowed to cool and stand overnight at room temperature. Water and 10% aq. NaOH was added dropwise, filtered. The filtrate was concentrated in vacuum to give the crude product, which was used directly without purification (1.15 g, crude). 1H-NMR (CDCl3): 5.06 (m, 4H), 5.23 (m, 2H), 7.42 (m, 2H), 7.60 (m, 2H), 7.82 (m, 2H). The result reaction mixture was refluxed for 3 h to cool filtered The filtrate was concentrated in vacuum

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-L 3-neck flask equipped with an overhead stirrer, a condenser, and a thermocouple was charged with (8-hydroxymethyl-naphthalen-1-yl)-methanol (33.0 g, 0.175 mol), concentrated phosphoric acid (225 mL), and water (5 mL). The reaction mixture was stirred at 140° C. for 3 h, cooled to room temperature, diluted with CH2Cl2 (800 mL) and transferred to a 2-L separatory funnel. After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 and evaporated to yield 1H,3H-Benzo[de]isochromene as a solid. A 1-L 3-neck flask equipped with an overhead stirrer, a condenser cooled to room temperature transferred to a 2-L separatory funnel After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addition funnel over 1.5 h. The solution was then heated to 95° C. overnight, cooled to 15° C. and then slowly diluted with ethyl acetate (2.2 L) and H2O (2 L) followed by addition of concentrated HCl (320 mL). The resulting suspension was stirred for 30 min at room temperature, filtered, and air dried on the filter for 2 h. The resultant material was in 95% ethanol (1.2 L), stirred at 70° C. for 2 h, and filtered to yield a wet solid which was air dried overnight on the filter and then dried at 70° C. in a vacuum oven to yield (8-hydroxymethyl-naphthalen-1-yl)-methanol as a solid; A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer cooled to 15° C. The resulting suspension was stirred for 30 min at room temperature filtered air dried on the filter for 2 h stirred at 70° C. for 2 h filtered to yield a wet solid which dried overnight on the filter dried at 70° C. in a vacuum oven

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-L 3-neck flask equipped with an overhead stirrer, a condenser, and a thermocouple was charged with (8-hydroxymethyl-naphthalen-1-yl)-methanol (33.0 g, 0.175 mol), concentrated phosphoric acid (225 mL), and water (5 mL). The reaction mixture was stirred at 140° C. for 3 h, cooled to room temperature, diluted with CH2Cl2 (800 mL) and transferred to a 2-L separatory funnel. After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 and evaporated to yield 1H,3H-Benzo[de]isochromene as a solid. A 1-L 3-neck flask equipped with an overhead stirrer, a condenser cooled to room temperature transferred to a 2-L separatory funnel After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addition funnel over 1.5 h. The solution was then heated to 95° C. overnight, cooled to 15° C. and then slowly diluted with ethyl acetate (2.2 L) and H2O (2 L) followed by addition of concentrated HCl (320 mL). The resulting suspension was stirred for 30 min at room temperature, filtered, and air dried on the filter for 2 h. The resultant material was in 95% ethanol (1.2 L), stirred at 70° C. for 2 h, and filtered to yield a wet solid which was air dried overnight on the filter and then dried at 70° C. in a vacuum oven to yield (8-hydroxymethyl-naphthalen-1-yl)-methanol as a solid; A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer cooled to 15° C. The resulting suspension was stirred for 30 min at room temperature filtered air dried on the filter for 2 h stirred at 70° C. for 2 h filtered to yield a wet solid which dried overnight on the filter dried at 70° C. in a vacuum oven