[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[CH:13]=[C:14](Cl)C=O)([O-:5])=[O:4].S(=O)(=O)(O)O>O1CCOCC1>[C:13]([C:12]1[CH:11]=[C:10]([CH:20]=[CH:19][CH:18]=1)[O:9][C:8]1[CH:21]=[CH:22][C:23]([N+:24]([O-:26])=[O:25])=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)#[CH:14]To 50 ml of refluxing 1N sodium hydroxide solution, under a nitrogen atmosphere, was added a solution containing 10 g (0.028 mole) of m-(3,4-dinitrophenoxy)-α-chlorocinnamaldehyde dissolved in 50 ml of 1,4-dioxane. The dark mixture was refluxed for one-half hour at which time the solution was cooled and acidified with 10% sulfuric acid. The reaction mixture was extracted with several 50 ml portions of ether, and the combined extracts evaporated to dryness. The residue was chromatographed on a 1 × 12 inch dry column of silica gel. Elution of the column using 3/1 hexane/methylene chloride produced a first band of sideproduct. Further elution using 1/1 hexane/methylene chloride yielded a second band which contained the desired product. Evaporation of the eluate to dryness in vacuo afforded 2 g (25%) of 4-(3-ethynylphenoxy)-o-dinitrobenzene as light yellow crystals, m.p. 68°-69°C.
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