5-methoxynaphthalene-1,4-dione

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

Procedure: 10 ml of hexyl alcohol and 50 ml of acetonitrile were placed in a 1 l three-necked flask, and 12.8 g of phosphorus oxychloride was dropwisely added thereto under cooling with ice while stirring. Thereafter, 9.5 g of SnCl2.2H2O was added to the reaction mixture at room temperature. Then, 7.5 g of 8-methoxy-1,4-naphthoquinone was added to the reaction mixture at room temperature. The reaction mixture was refluxed for 2 hours on steam bath. The reaction mixture was poured into 1.2 l of diluted hydrochloric acid and extracted with 500 ml of ethyl acetate. The ethyl acetate solution was washed with water, dried with MgSO4 overnight, and concentrated under reduced pressure to obtain 9 g of oily substance. The oily substance was purified by column chromatography using a mixed solvent of n-hexane and ethyl acetate and, then, recrystallized from benzene to obtain 6 g of white crystals having a melting point of 105° to 107° C. under cooling with ice The reaction mixture was refluxed for 2 hours on steam bath extracted with 500 ml of ethyl acetate The ethyl acetate solution was washed with water dried with MgSO4 overnight concentrated under reduced pressure to obtain 9 g of oily substance The oily substance was purified by column chromatography recrystallized from benzene

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

Procedure: 10 ml of hexyl alcohol and 50 ml of acetonitrile were placed in a 1 l three-necked flask, and 12.8 g of phosphorus oxychloride was dropwisely added thereto under cooling with ice while stirring. Thereafter, 9.5 g of SnCl2.2H2O was added to the reaction mixture at room temperature. Then, 7.5 g of 8-methoxy-1,4-naphthoquinone was added to the reaction mixture at room temperature. The reaction mixture was refluxed for 2 hours on steam bath. The reaction mixture was poured into 1.2 l of diluted hydrochloric acid and extracted with 500 ml of ethyl acetate. The ethyl acetate solution was washed with water, dried with MgSO4 overnight, and concentrated under reduced pressure to obtain 9 g of oily substance. The oily substance was purified by column chromatography using a mixed solvent of n-hexane and ethyl acetate and, then, recrystallized from benzene to obtain 6 g of white crystals having a melting point of 105° to 107° C. under cooling with ice The reaction mixture was refluxed for 2 hours on steam bath extracted with 500 ml of ethyl acetate The ethyl acetate solution was washed with water dried with MgSO4 overnight concentrated under reduced pressure to obtain 9 g of oily substance The oily substance was purified by column chromatography recrystallized from benzene

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

Procedure: 10 ml of hexyl alcohol and 50 ml of acetonitrile were placed in a 1 l three-necked flask, and 12.8 g of phosphorus oxychloride was dropwisely added thereto under cooling with ice while stirring. Thereafter, 9.5 g of SnCl2.2H2O was added to the reaction mixture at room temperature. Then, 7.5 g of 8-methoxy-1,4-naphthoquinone was added to the reaction mixture at room temperature. The reaction mixture was refluxed for 2 hours on steam bath. The reaction mixture was poured into 1.2 l of diluted hydrochloric acid and extracted with 500 ml of ethyl acetate. The ethyl acetate solution was washed with water, dried with MgSO4 overnight, and concentrated under reduced pressure to obtain 9 g of oily substance. The oily substance was purified by column chromatography using a mixed solvent of n-hexane and ethyl acetate and, then, recrystallized from benzene to obtain 6 g of white crystals having a melting point of 105° to 107° C. under cooling with ice The reaction mixture was refluxed for 2 hours on steam bath extracted with 500 ml of ethyl acetate The ethyl acetate solution was washed with water dried with MgSO4 overnight concentrated under reduced pressure to obtain 9 g of oily substance The oily substance was purified by column chromatography recrystallized from benzene