1-Methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene → 3,3,3-Trifluoro-2,2-dimethylpropanoic acid

To a biphasic mixture of 1-methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene (10.0 g, 45.8 mmol) and sodium periodate (137 g, 642 mmol) in a mixture solvent of CCl4:CH3CN:H2O (2:2:3, 550 ml) was added slowly ruthenium(III) chloride hydrate (0.517 g, 2.29 mmol) (black powder) while the reaction flask was kept in an ice-water bath. The mixture turned yellow rapidly then red after 5 minutes, ans was stirred for 0.5 h. The ice-water bath was removed and the reaction mixture was stirred vigorously, via a mechanical stirrer, overnight. The solids were filtered off, washed with 100 ml of DCM, 100 ml of H2O. The filtrate (pH ˜1) was basified with 10 N NaOH to pH >11, and the layers were separated, and the aq. layer was extracted with 130 ml of DCM. The aq. layer was then acidified carefully with conc. HCl to pH ˜1, extracted with 3×150 ml of DCM. The org layers were combined, dried (Na2SO4), and concentrated to give the title compound as an oil, which became a semi-solid upon drying on the vac line.

1. customwas kept in an ice-water bath
2. customThe ice-water bath was removed
3. stirringthe reaction mixture was stirred vigorously, via a mechanical stirrer, overnight
4. filtrationThe solids were filtered off
5. washwashed with 100 ml of DCM, 100 ml of H2O
6. customthe layers were separated
7. extractionthe aq. layer was extracted with 130 ml of DCM
8. extractionextracted with 3×150 ml of DCM
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated

ORD record

ord-809e141d93a9476babcef5e948082655

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633315B2