2,3-Dimethoxy-1,4-naphthoquinone

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: To 0.64 g (4.71 mmoles) of ZnCl2 in 50 mL of THF was added 7.0 g (0.697 mmoles/g in THF, 4.88 mmoles) of dodecyl MgBr. This mixture was added dropwise to 1.00 g (4.67 mmoles) of 2,3-dimethoxy-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight and worked up as in Example 30. Thus, 0.223 g (0.626 mmoles, 13.4%) of 2-methoxy-3-dodecyl-1,4-naphthoquinone was obtained, mp: 61° to 63° C. 1H NMR (δ, CDCl3): 8.05 (m,2H), 7.65 (m,2H), 4.10 (s,3H), 2.55 (m,2H), 1.30 (br s,20H), 0.85 (m,3H). IR (cm-1, KBr): 2950w, 2918s, 2842m, 1666s, 1642m, 1608m, 1589m, 1571w, 1462m, 1338m, 1329m, 1261m, 1255w, 1209m.

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

Procedure: To 0.216 g (1.62 mmoles) of AlCl3 in 50 mL of THF was added 7.0 g (0.697 mmoles/g in THF, 4.88 mmoles) of dodecyl MgBr. This mixture was added dropwise to 1.27 g (9.34 mmoles) of ZnCl2 and 1.00 g (4.67 mmoles) of 2,3-dimethoxy-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight, poured into 100 mL of NH4Cl solution, extracted with 3×50 mL of ether, dried over MgSO4, filtered, and solvent was removed by rotary evaporation. The residue was chromatographed on silica gel eluted with toluene. Thus, 0.034 g (0.096 mmoles, 2.1%) of 2-methoxy-3-dodecylnaphthoquinone was obtained. extracted with 3×50 mL of ether dried over MgSO4 filtered solvent was removed by rotary evaporation The residue was chromatographed on silica gel eluted with toluene

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether

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

Procedure: A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C. the mixture was evaporated The residue was dissolved in ether (100 mL) was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL) The organic layer was dried over sodium sulfate filtered evaporated Recrystallization from ether