Acetic Acid → 2'-Hydroxy-5'-nitroacetophenone
Reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N+:11]([O-])([OH:13])=[O:12].C(O)(=[O:17])C>>[CH3:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:17])=[O:4]Participants
Conditions
- Temperature
- 35 °C
Procedure
2-Hydroxyacetophenone (25.0 g, 183.62 mmol) (B6) was taken up in acetic acid (150 mL) and heated to 35° C. To this solution was then added concentrated nitric acid (26 mL) dropwise over 1.5 hours. After the addition the reaction mixture was stirred overnight at room temperature and worked up by pouring into ice water. The oil so obtained was extracted with ethyl acetate. The ethyl acetate layer was then dried (MgSO4), filtered, concentrated to an oil under reduced pressure and coevaporated with heptane to remove residual acetic acid. The residue was taken up in 50% dichloromethane in heptane and subjected to flash chromatography eluting with the same solvent mixture. The first major band was collected and concentrated to give the desired 2-hydroxy-5-nitroacetophenone, yield 12.0 g (39%). The 2-hydroxy-3-nitroacetophenone isomer was also formed in this reaction and could readily be isolated from the same chromatography column.
Workup
- additionAfter the addition the reaction mixture
- customThe oil so obtained
- extractionwas extracted with ethyl acetate
- dry with materialThe ethyl acetate layer was then dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to an oil under reduced pressure
- customto remove residual acetic acid
- washeluting with the same solvent mixture
- customThe first major band was collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cc1714148b4844d080bfa0709507af74
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05021322
Reaction notes
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