Réaction #560543

Équation de réaction

1-methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene

sodium periodate

CCl4 CH3CN H2O

→

title compound

3,3,3-Trifluoro-2,2-dimethylpropanoic acid

Conditions de réaction

Traitement

1. 1
   Autrewas kept in an ice-water bath
2. 2
   AutreThe ice-water bath was removed
3. 3
   workup.STIRRINGthe reaction mixture was stirred vigorously, via a mechanical stirrer, overnight
4. 4
   FiltrationThe solids were filtered off
5. 5
   Lavagewashed with 100 ml of DCM, 100 ml of H2O
6. 6
   Autrethe layers were separated
7. 7
   Extractionthe aq. layer was extracted with 130 ml of DCM
8. 8
   Extractionextracted with 3×150 ml of DCM
9. 9
   Séchagedried (Na2SO4)
10. 10
    Concentrationconcentrated

Mode opératoire

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.

Source