1,4-dimethylanthracene-9,10-dione

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 1 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit1. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 1 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit1. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 11 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 11 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 11 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 11 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2 H, s), 8.06 (2 H, dd, J=6.5 and 3.3 Hz), 7.50 (2 H, dd, J=6.5 and 3.3 Hz), 7.22 (2 H, s), 2.82 (6 H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol

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

Procedure: To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 1 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit1. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2H, s), 8.06 (2H, dd, J=6.5 and 3.3 Hz), 7.50 (2H, dd, J=6.5 and 3.3 Hz), 7.22 (2H, s), 2.82 (6H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight quenched by pouring into 5% HCl solution The mixture was left to stir for 1 hr the solution was filtered to give a yellow solid The solid was further recrystallized from ethanol