C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]1[CH2:21][C:22]([OH:24])=[O:23]>C(O)(=O)C>[N+:8]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH2:12][CH:13]([CH2:21][C:22]([OH:24])=[O:23])[CH2:14]2)([O-:11])=[O:9]Acetic anhydride (3.5 mL) was added slowly to a stirred solution of nitric acid (2.1 g, S.G.1.42) in glacial acetic acid (4.2 mL) cooled in an ice-water bath. This nitrating solution was then added dropwise over 5 minutes to a rapidly stirred solution of indan-2-acetic acid (1.65 g) in a mixture of glacial acetic acid (4.2 mL) and acetic anhydride (3.5 mL), whilst keeping the reaction temperature below 5° C. After stirring for a further 20 minutes at room temperature the reaction mixture was poured onto ice-water (60 mL). This mixture was extracted three times with dichloromethane. The combined extracts were washed twice with a little water, then dried over magnesium sulfate and then evaporated to give the title compound (2.22 g) as a red oil which was used without further purification.
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