[BH4-].[Na+].[Cl:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:15])[C:5]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.Cl>CO>[Cl:3][C:4]1[C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[C:6]([OH:15])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=21 g of sodium borohydride was added, whilst ice-cooling, to a solution of 11 g of 3-chloro-2-(4-nitrophenoxy)-1,4-naphthoquinone (prepared as described in Preparation 17) in 150 ml of methanol, and the mixture was stirred, whilst ice-cooling, for 30 minutes. The mixture was then poured into a mixture of ice and 15 ml of 2N aqueous hydrochloric acid to give a precipitate, which was collected by filtration, washed with water and dried under reduced pressure in the presence of phosphorus pentoxide, to give 9 g of 3-chloro-1,4-dihydroxy-2-(4-nitrophenoxy)naphthalene.
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