Hydrochloric Acid → 4-N-Propylphenylacetic Acid
Reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[CH:6][CH:5]=1)[CH2:2][CH3:3].Cl.S([O-])([O-])(=O)=[O:15].[Mg+2].[OH-:20].[Na+]>>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:15])=[O:20])=[CH:6][CH:5]=1)[CH2:2][CH3:3]Participants
5
Procedure
2-(4-propylphenyl)acetonitrile (41.0 mg, 0.257 mmol) was dissolved in 1 mL of 30% aqueous sodium hydroxide solution and stirred under reflux condition for 4 hours. Upon completion of the reaction, the reaction solution was acidified by adding 3 mL of 10% aqueous hydrogen chloride solution and extracted with diethyl ether (3 mL×3). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 34.8 mg (0.195 mmol, 76%) of the desired compound (balance unit of tag β).