Methanol → 2-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:21][CH3:22])=[C:12]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:13]=2)=[CH:4][CH:3]=1.CO.[OH-].[K+].CCCCCC>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:21][CH3:22])=[C:12]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:13]=2)=[CH:6][CH:7]=1Participants
Procedure
To a 50 ml volume three-necked flask, ethyl 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetate (9-c) (1.43 g), methanol (1.9 ml), and potassium hydroxide (600 mg) dissolved in water (3 ml) were added at room temperature, then added methanol (7.6 ml) and water (3 ml), and stirred at 40° C. for 2 hours. To the mixture was added hexane and 2N aqueous potassium hydroxide solution (3 ml), and then the layers were separated. The aqueous layer was washed with hexane again. The organic layers were combined, and extracted with 2N potassium hydroxide. To the resulting aqueous layer, 10 w/w % of hydrochloric acid was added to adjust pH to less than 1, and extracted with ethyl acetate times. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 1.081 g of 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetic acid (8-c).
Workup
- additionwere added at room temperature
- customthe layers were separated
- washThe aqueous layer was washed with hexane again
- extractionextracted with 2N potassium hydroxide
- additionTo the resulting aqueous layer, 10 w/w % of hydrochloric acid was added
- extractionextracted with ethyl acetate times
- washwashed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cf1a64964e114156a508a5f5f60f3402
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08884010B2
Reaction notes
Loading…