Water → 1,1-Dimethylethyl 2-methyl-5-(trifluoromethyl)benzoate
Reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][C:8]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:9]=1[C:10](Cl)=[O:11].O>O1CCCC1>[CH3:7][C:8]1[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:9]=1[C:10]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:11]Participants
Procedure
Potassium tert-butoxide (5.40 g, 48.1 mmol) was added to an ice-cooled solution of 2-methyl-5-trifluoromethylbenzoyl chloride (10.5 g, 47.2 mmol) (manufactured by Apollo Scientific Inc.) in tetrahydrofuran (180 ml) in a small portion and the mixture was stirred for 1 hour. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with a 5% aqueous sodium hydrogencarbonate solution, water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=60/1-20/1) to give tert-butyl 2-methyl-5-(trifluoromethyl)benzoate as a colorless oil (9.90 g, yield: 81%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washthe organic layer was successively washed with a 5% aqueous sodium hydrogencarbonate solution, water (twice) and a saturated aqueous NaCl solution
- dry with materialdried with anhydrous sodium sulfate
- customThe residue obtained
- customby removing the solvent under reduced pressure
- customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=60/1-20/1)
Sources & evidence
- ORD record
- ord-bbd96c6d824948aa871c3d6409a6e5fe
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923573B2
Reaction notes
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