Potassium Hydroxide → 2-(2-Ethylphenyl)acetic acid
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]=[O:11])[CH3:2].[OH-:12].[K+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11])[CH3:2]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the crude (2-ethylphenyl)acetaldehyde in 20 ml of EtOH was added a solution of 2.29 g (13.52 mmol) of AgNO3 in 7.5 ml of water and a solution of 2.08 g (37.2 mmol) of KOH in 13 ml of water at 0° C. The reaction mixture was stirred at 0° C. for 2 h and was filtered to remove the precipitated silverhydroxide. The filtrate was extracted with CH2Cl2 (20 ml×3) and the organic fractions were discarded. The aqueous layer was acidified with 6N HCl to PH=1 and was extracted with CH2Cl2 (50 ml×3). The combined organic layers were dried over MgSO4 and concentrated to give 2-ethylphenylacetic acid.
Workup
- customat 0° C
- filtrationwas filtered
- customto remove the precipitated silverhydroxide
- extractionThe filtrate was extracted with CH2Cl2 (20 ml×3)
- extractionwas extracted with CH2Cl2 (50 ml×3)
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5e4b34efd73b4df8a19dfe4d8e54a1dc
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06083980
Reaction notes
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