Acetone → 2,3-Dimethoxy-6-nitrobenzoic acid

HRID 580037Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:4]=1[CH:5]=[O:6].CC(C)=[O:18].[Mn]([O-])(=O)(=O)=O.[K+].C(O)(C)C>O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:4]=1[C:5]([OH:18])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

2,3-Dimethoxy-6-nitrobenzaldehyde (40.0 g, 0.19 mole) was treated with acetone (275 mL) and warmed to 50° C. A solution of potassium permanganate in water (60 g/L) was added slowly at 50°-70° C. over a period of 16-20 hours until thin layer chromatographic analysis revealed complete absence of the starting material. Isopropanol (7.5 mL) was then added and the mixture was heated an additional hour. The precipitated manganese dioxide was removed by filtration and the filter cake was washed with 3% aqueous potassium hydroxide (ca 175-200 mL). The combined filtrates were acidified with hydrochloric acid and the precipitate was collected by filtration and dried in vacuo. The crude product was recrystallized from acetone to give the pure material, 28.3 g (67%), mp 187°-189° C.).

Workup

temperaturethe mixture was heated an additional hour
customThe precipitated manganese dioxide was removed by filtration
washthe filter cake was washed with 3% aqueous potassium hydroxide (ca 175-200 mL)
filtrationthe precipitate was collected by filtration
customdried in vacuo
customThe crude product was recrystallized from acetone
customto give the pure material, 28.3 g (67%), mp 187°-189° C.)

Sources & evidence

ORD record: ord-dc1f9ff723fe456abcd1879a0c9c9107
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751304

Reaction notes

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