Nitric Acid → 6-methoxy-2,2-dimethyl-7-nitro-2H-1-benzopyran

HRID 2425355Notes

Reaction equation

C(OC(=O)C)(=O)C.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[CH:16]=[CH:15][C:14]=2[CH:21]=1.[N+:22]([O-])([OH:24])=[O:23].[OH-].[Na+]>C(O)(=O)C>[CH3:8][O:9][C:10]1[C:11]([N+:22]([O-:24])=[O:23])=[CH:12][C:13]2[O:18][C:17]([CH3:19])([CH3:20])[CH:16]=[CH:15][C:14]=2[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixed solution of acetic acid (6.2 mL) and acetic anhydride (6.2 mL) containing 6-methoxy-2,2-dimethyl-2H-1-benzopyran (3.1 g, 16.4 mmol) was cooled with ice, nitric acid (1.37 mL, 18.0 mmol) was added dropwise and then the mixture was stirred at 0° C. for 1 hour. Upon the completion of the reaction, an aqueous solution of 1 mol/L sodium hydroxide was added to the reaction solution, the resulting solution was extracted with ethyl acetate (150 mL). The organic phase was washed twice with 1 mol/L sodium hydroxide aqueous solution and once with saturated sodium chloride solution. Then, the organic phase was dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=6/1) and the aimed product was obtained as yellow crystal (yield: 79%).

Workup

additionwas added dropwise
customUpon the completion of the reaction
extractionthe resulting solution was extracted with ethyl acetate (150 mL)
washThe organic phase was washed twice with 1 mol/L sodium hydroxide aqueous solution and once with saturated sodium chloride solution
dry with materialThen, the organic phase was dried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record: ord-8f0f3cac80524d39af15cc216a16fd8a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964623B2

Reaction notes

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