Nitric Acid → 6-(4-Nitrophenyl)hexanoic acid
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:15]([O-])([OH:17])=[O:16]>C(OCC)(=O)C.CCCCCC>[N+:15]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2][CH:3]=1)([O-:17])=[O:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
6-Phenylhexanoic acid (30 g) was added dropwise over 6.5 hours to 125 ml of 90% nitric acid with cooling to -30° to -20° C. When the addition was complete, the mixture was allowed to warm to -10° C. for 30 minutes and it was then poured into ice water. The resulting mixture was extracted with diethyl ether and the ether extract was washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then evaporated to leave a crude yellow solid which was subjected to high pressure liquid chromatography using ethyl acetate/hexane/glacial acetic acid as the eluent. This chromatography removed dinitrated material and gave a yellow slush which was recrystallized from a mixture of toluene and hexane to give 6-(4-nitrophenyl)hexanoic acid.
Workup
- temperaturewith cooling to -30° to -20° C
- additionWhen the addition
- extractionThe resulting mixture was extracted with diethyl ether
- extractionthe ether extract
- washwas washed with water and saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvent was then evaporated
- customto leave a crude yellow solid which
- customThis chromatography removed
- customgave a yellow slush which
- customwas recrystallized from a mixture of toluene and hexane
Sources & evidence
- ORD record
- ord-b7f01541874947c3817afdd38da72f7c
- Source dataset
- uspto-grants-1983_07
- Patent number
- US04391818
Reaction notes
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