Potassium Permanganate → 2-[(1,1-Dimethylethyl)oxy]-6-chlorobenzoic acid
Reaction equation
[CH3:1][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[CH:8]=[O:9])([CH3:4])[CH3:3].[OH:15]P([O-])(O)=O.[K+].[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(C)(C)C>[CH3:4][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[C:8]([OH:15])=[O:9])([CH3:1])[CH3:3]Participants
Procedure
To a solution of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzaldehyde (8.40 g, 40.0 mmol) in t-butanol (200 mL) was added 1.25M KH2PO4 (pH 7, 200 mL) and 0.4M aqueous potassium permanganate (200 mL, 80 mmol). The reaction was stirred at room temperature for 3 h and was quenched by the addition of saturated aqueous sodium sulfite (200 mL). The brown suspension was acidified with 2N HCl with ice-cooling until the MnO2 dissolved (pH 4). The reaction was extracted with ethyl acetate (3 times) and the organic layers were washed with brine, dried (MgSO4) and concentrated to a white solid. The crude product was recrystallized from hexanes at 0° C. to afford 7.14 g (78%) of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzoic acid as white crystals: mp 117°-119° C.
Workup
- customwas quenched by the addition of saturated aqueous sodium sulfite (200 mL)
- temperaturecooling until the MnO2
- dissolutiondissolved (pH 4)
- extractionThe reaction was extracted with ethyl acetate (3 times)
- washthe organic layers were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated to a white solid
- customThe crude product was recrystallized from hexanes at 0° C.
Sources & evidence
- ORD record
- ord-49103b2092984fb4bd2ab72070fd6d7b
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05482974
Reaction notes
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