Hydrochloric Acid → Methyl 2-hydroxy-2-[4-(trifluoromethyl)phenyl]acetate

To a mixture of 4-(trifluoromethyl)benzaldehyde (500 μL, 3.66 mmol) and trimethylsilyl cyanate (537 μL, 4.03 mmol), lithium chloride (a 0.307 mol/L solution in tetrahydrofuran, 1.2 μL, 0.366 μmol) was added and the mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The reaction mixture was diluted with diethyl ether (10 mL). To this, a 10% solution of hydrogen chloride in methanol (10 mL) was added at 0° C. and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated, water was added thereto, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give methyl hydroxy-4-(trifluoromethyl)phenylacetate (Compound CH) (587 mg, yield: 68%).

1. additionwas added
2. stirringthe mixture was stirred at room temperature for 24 hours
3. concentrationThe reaction mixture was concentrated
4. additionwater was added
5. extractionextraction with ethyl acetate
6. washby washing with brine
7. dry with materialdrying over anhydrous sodium sulfate
8. customThe solvent was evaporated off under reduced pressure
9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

ORD record

ord-994ca3225180400eb59f4ff12ac27732

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2