Ethanol → 3-Chloro-5-methylphenylethyl acetate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-:12].[Na+].S(=O)(=O)(O)O.[CH2:19]([OH:21])[CH3:20]>>[C:19]([O:12][CH2:10][CH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:20]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To [(3-chloro-5-methylphenyl)]acetonitrile (0.38 g; 2.29 mmol) were added 2N aqueous sodium hydroxide solution (2.1 ml) and ethanol (5 ml). The mixture was stirred at 80° C. for 1 hour. The reaction solution was concentrated under reduced pressure. To the residue were added water and 2N-aqueous HCl to become neutral. Ethyl acetate was added thereto and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure to give colorless crystal. Concentrated sulfuric acid (0.02 ml) and ethanol (2 ml) were added thereto, and the mixture was refluxed for 5 hours. The reaction solution was concentrated under reduced pressure. To the residue were added water and 2N-aqueous sodium hydroxide solution to become neutral. Ethyl acetate was added thereto and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1) to give 3-chloro-5-methylphenylethyl acetate as colorless oil (0.31 g; 63%).