[OH-].[K+].C(=O)(OC)[O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:6]=1[Cl:18].Cl>CO>[C:14]([C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([OH:4])=[C:6]([Cl:18])[CH:7]=1)([CH3:17])([CH3:15])[CH3:16]Potassium hydroxide (10.1 g, 181 mmol) was added to 4-tert-butyl-2-chloro-5-nitrophenyl methyl carbonate (40.0 g, 139 mmol) in MeOH (100 mL). After 30 min, the reaction was acidified with 1N HCl and extracted with dichloromethane. The combined organic layers were combined, dried over Na2SO4 and concentrated under vacuum. The crude residue was purified by column chromatography (Pet. Ether/EtOAc, 30:1) to give 4-tert-butyl-2-chloro-5-nitro-phenol (23.0 g, 68% over 2 steps).
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