Water → HCID 56851158, compound

HRID 1690775Notes

Reaction equation

HRID 1690775 reaction equation
[F:1][C:2]([F:7])([F:6])[C@@H:3]([OH:5])[CH3:4].[H-].[Na+].F[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].O>O1CCOCC1>[F:1][C:2]([F:7])([F:6])[C@H:3]([CH3:4])[O:5][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 99352-Fluorobenzoic acidHCID 24758Sodium hydrideHCID 6999971(2S)-1,1,1-Trifluoropropan-2-ol

Product 1

HCID 56851158HCID 56851158, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

36.0 g (316 mmol) of (S)-1,1,1-trifluoro-propan-2-ol (CAS: 3539-97-7) was added to a cold (0 to 5° C.) suspension of 17.0 g (425 mmol) of NaH (pract., 60%) in 200 ml of dioxane. The suspension was stirred at room temperature during 0.5 h then cooled (0 to 5° C.) and a solution of 20.0 g (143 mmol) of 2-fluoro-benzoic acid in 100 ml of dioxane was added. The mixture was stirred during 0.5 h at room temperature and during 140 h under reflux. The mixture was poured into 800 ml of water, washed with 300 ml of MTBE, then acidified to pH 2 with hydrochloric acid and the product was extracted with MTBE. The solvent was concentrated in vacuo and the residue was crystallized from ethanol/water to provide 27.3 g (82%) of the title compound as a white solid. MS (m/e): 234.1 [M]+.

Workup

  1. temperaturethen cooled (0 to 5° C.)
  2. stirringThe mixture was stirred during 0.5 h at room temperature and during 140 h
  3. temperatureunder reflux
  4. washwashed with 300 ml of MTBE
  5. extractionthe product was extracted with MTBE
  6. concentrationThe solvent was concentrated in vacuo
  7. customthe residue was crystallized from ethanol/water

Sources & evidence

ORD record
ord-d9ff7e9ecaae4240af83d4cc2e6b6a29
Source dataset
uspto-grants-2012_04
Patent number
US08153679B2

Reaction notes

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