Sodium Hydroxide → 3-(5-Fluoro-2-methylphenyl)-3-methylbutanoic acid
Reaction equation
FC(F)(F)[C:3](=[O:16])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH3:15])([CH3:7])[CH3:6].[OH-:19].[Na+]>O.C(O)C>[F:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:5]([CH3:6])([CH3:7])[CH2:4][C:3]([OH:16])=[O:19])[CH:13]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
A solution of 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one (4.88 g, 18.6 mmol) was treated with sodium hydroxide solution (4 M in a mixture of 30% water in ethanol, 40 mL) at room temperature. The mixture was heated to 80° C. for 1 hour. After cooling to room temperature, the mixture was diluted with 100 mL of water and extracted with three 100 mL portions of diethyl ether. The aqueous layer was treated with 150 mL of ethyl acetate and the resulting mixture was treated with 6 M HCl dropwise until the solution had a pH of 2. The phases were separated and the aqueous layer was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 3.92 g of 3-(5-fluoro-2-methylphenyl)-3-methylbutyric acid as an oil, which solidified upon standing and was used without further purification (quantitative yield).
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with three 100 mL portions of diethyl ether
- additionThe aqueous layer was treated with 150 mL of ethyl acetate
- additionthe resulting mixture was treated with 6 M HCl dropwise until the solution
- customThe phases were separated
- extractionthe aqueous layer was extracted with three 100 mL portions of ethyl acetate
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cbe7510bc25b49a5bf4c25d8a063843b
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741897B2
Reaction notes
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