Methanol → 4-(Pentan-2-yl)benzoic acid
Reaction equation
[CH3:1][CH:2]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].O1CCCC1.CO>O>[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)[CH2:3][CH2:4][CH3:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture of methyl 4-(pentan-2-yl)benzoate (634 mg, 3.1 mmol), lithium hydroxide monohydrate (646 mg, 15.4 mmol), tetrahydrofuran (12.0 mL), methanol (4.0 mL) and water (4.0 mL) was stirred at 20° C. for 4 hours. The mixture was acidified to pH=3-4. The mixture was extracted with ethyl acetate (20 ml×3). The organic phase was dried by sodium sulfate. The mixture was filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, petroleum/ethyl acetate=6:1) to gave 4-(pentan-2-yl)benzoic acid (E1-c) as a white solid (487 mg, 82%). LRMS (M−H)− m/z: 192.12. found 192.
Workup
- extractionThe mixture was extracted with ethyl acetate (20 ml×3)
- dry with materialThe organic phase was dried by sodium sulfate
- filtrationThe mixture was filtered
- concentrationThe filtrate was concentrated
- customthe residue was purified by column chromatography (silica gel, petroleum/ethyl acetate=6:1)
Sources & evidence
- ORD record
- ord-d11513b5661340d7be5aef29bfb515f2
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051269B2
Reaction notes
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