Potassium Permanganate → 2-Chloro-6-(difluoromethoxy)benzoic acid
Reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH:15]([F:17])[F:16])[C:9]=1[CH3:18].S(S([O-])=O)([O-])(=O)=[O:20].[Na+].[Na+].C(O)(C)(C)C.[OH2:33]>>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH:15]([F:16])[F:17])[C:9]=1[C:18]([OH:20])=[O:33]Participants
Conditions
- Temperature
- 100 °C
Procedure
Potassium permanganate (1.64 g) was added portionwise over a period of 4 hours to a stirred mixture of 1-chloro-3-[(difluoromethyl)oxy]-2-methylbenzene (0.999 g) in t-butanol/water (20 ml, 1:1) heated at 100° C. The reaction mixture was heated for a further 4 hours—total heating time was 8 hours. The reaction mixture was allowed to cool to room temperature and then allowed to stand overnight. Aqueous sodium metabisulphite solution (5%) was added dropwise until the purple colour disappeared and the resultant mixture was filtered. The filtrate was adjusted to pH 10 using aqueous sodium carbonate solution and extracted with ether (100 ml). The aqueous portion was acidified using aqueous hydrochloric acid (2M) to pH 1 and then extracted with ether (100 ml). The ether layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), filtered and evaporated. The title compound was obtained as a colourless oil (0.538 g).
Workup
- temperatureThe reaction mixture was heated for a further 4 hours—total heating time
- temperatureto cool to room temperature
- waitto stand overnight
- filtrationthe resultant mixture was filtered
- extractionextracted with ether (100 ml)
- extractionextracted with ether (100 ml)
- washThe ether layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-9387f44d91c544ee9085971428a65ab2
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247377B2
Reaction notes
Loading…