Nitric Acid → 2-(2-Benzyloxy-5-nitrophenyl)-2-methylpropionic acid methyl ester

HRID 1861967Notes

Reaction equation

S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12](=[O:30])[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:15])[CH3:14].C(OCC)(=O)C>C(O)(=O)C>[CH3:10][O:11][C:12](=[O:30])[C:13]([C:16]1[CH:21]=[C:20]([N+:6]([O-:9])=[O:7])[CH:19]=[CH:18][C:17]=1[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of sulfuric acid (0.27 ml) and nitric acid (0.34 ml), a solution of the compound (1.0 g) obtained in Example 561 in acetic acid (30 ml) was added dropwise at 5° C. The reaction mixture was stirred at 45° C. for 4 h, poured into ice cold water and ethyl acetate was added to the mixture. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=9:1) to give 530 mg of the titled compound (yield, 46%).

Workup

additionwas added to the mixture
washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-5268074992f94beda50fb17d68ce791d
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534546B1

Reaction notes

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