Nitric Acid → Methyl 3-(4-carboxy-2-nitrophenyl)propionate
Reaction equation
ClC[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)=[O:4].[N+:17]([O-])([OH:19])=[O:18].S(=O)(=O)(O)[OH:22]>>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=1)([OH:4])=[O:22]Participants
Procedure
36.26 Grams of methyl 3-(4-chloroacetylphenyl)propionate was dissolved in 300 ml of concentrated sulfuric acid, then 20.9 g of fuming nitric acid (d=1.52) was added dropwise thereto under an ice-cooled condition with stirring. The reaction mixture was further stirred at a room temperature for 3 hours, then was poured into ice-water, and extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was purified by a silica gel column chromatography, then crystallized by adding ether. The crystals formed were collected by filtration, recrystallized from methanol to obtain 26.7 g of methyl 3-(4-carboxy-2-nitrophenyl)propionate in the form of light yellowish prism-like crystals.
Workup
- temperatureunder an ice-cooled condition
- stirringThe reaction mixture was further stirred at a room temperature for 3 hours
- extractionextracted with chloroform
- washThe chloroform layer was washed with water
- customdried
- customchloroform was removed by distillation
- customThe residue thus obtained
- customwas purified by a silica gel column chromatography
- customcrystallized
- additionby adding ether
- customThe crystals formed
- filtrationwere collected by filtration
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-9164240ce1e24274b2235a1b4ec02a40
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04578381
Reaction notes
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