[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>C(OCC)C>[C:17]([O:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])(=[O:19])[CH3:18]
A stirred mixture of (3-hydroxy-4-nitro-phenyl)acetic acid (1 2.0 g), aqueous sodium hydroxide (152.3 mL, 1M) and diethyl ether (150 mL), cooled to 0° C. in an ice salt bath, was treated dropwise with acetic anhydride (8.1 g) at a rate to maintain the temperature at 0° C. When the addition was complete the mixture was stirred at 0° C. for a further 2 hours then acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extracts were dried over magnesium sulphate and then evaporated to give the title compound (12.6 g) as an oil.
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