[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-:22])=[O:21])[CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:6]=[CH:7][CH:8]=1.Cl.[Cl-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-:22])=[O:21])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1
To a solution of tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate (10.00 g) in 1,4-dioxane (10 ml) was added 4N hydrogen chloride in 1,4-dioxane (17.8 ml) in an ice bath. After stirring for 3 days at ambient temperature, ice water (60 ml) and sodium chloride (6 g) was added to the solution. The pH of the solution was adjusted to 9.5 with an aqueous saturated sodium hydrogencarbonate solution and the solution was washed with ethyl acetate. After the pH of the solution was adjusted to 1 with 6N hydrochloric acid, the solution was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, treated with silica gel (20 g), and evaporated in vacuo to give 5-(3-methoxyphenyl)-4-nitrovaleric acid (8.00 g).
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