Nitric Acid → Methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate

To a mixture of methyl 4-(3-methoxy-3-oxopropyl)benzoate (10 g) and sulfuric acid (50 ml) was added dropwise fumed nitric acid (5.7 ml) under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into ice-water and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue were added methanol and concentrated sulfuric acid, followed by stirring at 105° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice-cooling. The resulting solid was collected by filtration and washed with a saturated aqueous sodium hydrogen carbonate solution and water to obtain methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate (12 g).

1. temperaturecooling
2. extractionextracted with chloroform
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. additionTo the residue were added methanol and concentrated sulfuric acid
7. stirringby stirring at 105° C. for 1 hour
8. concentrationThe reaction mixture was concentrated under reduced pressure
9. additiona saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice-
10. temperaturecooling
11. filtrationThe resulting solid was collected by filtration
12. washwashed with a saturated aqueous sodium hydrogen carbonate solution and water

ORD record

ord-2e4e7de5d1434149a91cb3ca833bf0db

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030489B2