Water → 1-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one

HRID 1295438Notes

Reaction equation

HRID 1295438 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([OH:8])=O.[CH2:18]1COCC1.C[Li].O>C(OCC)C>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]([C:6](=[O:8])[CH3:18])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 178418348HCID 178418348, compound2×

Product 1

HCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.16 g (20 mmol) of 3,5-bis(trifluoromethyl)benzoic acid were dissolved in 100 ml of abs. THF and admixed at 0° C. with 31.25 ml of a 1.6 M solution of methyllithium in diethyl ether. After the mixture had been stirred at room temperature for 5 hours, excess methyllithium was hydrolyzed by adding H2O and the solvent was removed in vacuo. The residue was taken up in dichloromethane and washed with saturated NaHCO3 solution. The organic phase was removed, dried over MgSO4 and concentrated. Chromatography on silica gel afforded 3.97 g of the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. washwashed with saturated NaHCO3 solution
  3. customThe organic phase was removed
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe8b43533e4a4b5b8fb06a24f1c7ca21
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Reaction notes

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