2-chloro-3-methylnaphthalene-1,4-dione

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

Procedure: A solution of 10% aqueous potassium hydroxide (150 mL) was added to a solution of 2-chloro-3-methyl-1,4-naphthoquinone (10.3 g) in refluxing methanol (500 mL). After cooling and acidification with concentrated hydrochloric acid, the precipitated product was collected by filtration to give 2-hydroxy-3-methyl-1,4-naphthoquinone, m.p. 173°-174° C. After cooling acidification with concentrated hydrochloric acid, the precipitated product was collected by filtration

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

Procedure: A solution of 2-chloro-3-methyl-1,4-naphthoquinone (10.3 g) in tetrahydrofuran (100 mL) was treated dropwise with a solution of sodium methoxide (320 g) in tetrahydrofuran (25 mL) at room temperature. After stirring overnight, the mixture was evaporated, and the residue was taken up in ether. The organic layer was washed with brine, dried, filtered and evaporated. Chromatography over silica gel gave 2-methoxy-3methyl-1,4-naphthoquinone, m.p. 93°-94° C. the mixture was evaporated The organic layer was washed with brine dried filtered evaporated