Hydrochloric Acid → 2-Methylbutanoic acid 4-(2-methylbutanoyl) biphenyl
Reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[N+]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=[O:14]>>[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:14])=[O:4].[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([C:19]1[CH:20]=[CH:21][C:16]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:17][CH:18]=1)=[O:4]Participants
Conditions
- Temperature
- 0 °C
Procedure
Then, 4.0 g of (+)-2-methylbutanoic acid chloride and 7 ml of nitrobenzene were charged into a flask and cooled to 0° C., to which was added 10.74 g (80 mmol) of aluminum chloride with stirring and further added a solution of 4.97 g (19.6 mmol) of (+) 2-methylbutanoic acid-4-biphenyl in 9 ml of nitrobenzene and then stirred at room temperature for 70 hours. Thereafter, the resulting mixture was added with 2 normal hydrochloric acid and ice and extracted with chloroform. The chloroform layer was washed with water, dried on anhydrous magnesium sulfate, and purified by a column chromatography of silica gel after the distillation off of the solvent to obtain 3.60 g (yield 54%) of oily 2-methylbutanoic acid-4-(2-methylbutanoyl) biphenyl. The NMR analytical values of this purified product were as follows.
Workup
- stirringstirred at room temperature for 70 hours
- extractionextracted with chloroform
- washThe chloroform layer was washed with water
- dry with materialdried on anhydrous magnesium sulfate
- custompurified by a column chromatography of silica gel
- distillationafter the distillation off of the solvent
Sources & evidence
- ORD record
- ord-58e799445db4465e80ac4d17f7d08dc9
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137653
Reaction notes
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