Water → 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

HRID 1860962Notes

Reaction equation

HRID 1860962 reaction equation
F[C:2](F)(F)S(O)(=O)=O.[C]=O.[F:11][C:12]([F:28])([F:27])[C:13]1[CH:14]=[C:15]([C:23](O)([CH3:25])[CH3:24])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.[OH-:29].[Na+].[OH2:31]>ClCCl>[F:11][C:12]([F:28])([F:27])[C:13]1[CH:14]=[C:15]([C:23]([CH3:2])([CH3:25])[C:24]([OH:31])=[O:29])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 6207792-[3,5-bis(trifluoromethyl)phenyl]propan-2-olHCID 178418416HCID 178418416, compound

Product 1

HCID 98359482-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 185 ml stainless steel autoclave was charged under argon with 25 ml of dichloromethane, 22.30 ml (0.25 mol) of trifluoromethane sulfonic acid and 0.45 ml (25 mmol) of water. The autoclave was sealed and pressurized with 30 bar of carbon monoxide. Then under stirring a solution of 14.13 g (50 mmol) of 2-(3,5-bis-trifluoromethyl-phenyl)-propan-2-ol in 35 ml of dichloromethane was added with a pump within 50 min at 20° C. and the reaction mixture was stirred for additional 2 h. Thereafter the autoclave was vented and the biphasic reaction mixture was treated in an ice bath with a solution of 13.2 g of sodium hydroxide in 130 ml of water. The organic phase was removed and the aqueous phase was washed with dichloromethane. After filtration, 35 ml of 36.5% hydrochloric acid solution were added to the aqueous phase under stirring at 8-12° C. The resulting suspension was extracted twice with dicloromethane and, after drying with sodium sulfate, the organic phase was evaporated and the solid residue dried at room temperature and 10 mbar vacuum. 14.98 g of 2-(3,5-bis-trifluoromethylphenyl)-2-methyl-propionic acid were isolated as light brown crystals with m.p. 105.5-107° C. and 99.0% purity according to HPLC analysis.

Workup

  1. customThe autoclave was sealed
  2. additionwas added with a pump within 50 min at 20° C.
  3. customthe biphasic reaction mixture
  4. customThe organic phase was removed
  5. washthe aqueous phase was washed with dichloromethane
  6. filtrationAfter filtration, 35 ml of 36.5% hydrochloric acid solution
  7. additionwere added to the aqueous phase
  8. stirringunder stirring at 8-12° C
  9. extractionThe resulting suspension was extracted twice with dicloromethane
  10. dry with materialafter drying with sodium sulfate
  11. customthe organic phase was evaporated
  12. customthe solid residue dried at room temperature

Sources & evidence

ORD record
ord-04c0bf0f189e49acb8dc9b6d020df6ea
Source dataset
uspto-grants-2003_03
Patent number
US06531597B2

Reaction notes

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