Hydrochloric Acid → 1-[3,5-Bis(trifluoromethyl)phenyl]propan-1-ol

HRID 1442520Notes

Reaction equation

HRID 1442520 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[O:7].[CH2:17]([Mg]Br)[CH3:18].Cl>O1CCCC1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 102363091-[3,5-Bis(trifluoromethyl)phenyl]propan-1-olYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)benzaldehyde (300 mg, 1.24 mmol) in anhydrous tetrahydrofuran (3 mL) stirred on an ice bath was added ethylmagnesium bromide (1.00 M solution in anhydrous tetrahydrofuran, 1.86 mL, 1.86 mmol), and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was added with 1 M hydrochloric acid on an ice bath until pH became 7 or lower, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-[3,5-bis(trifluoromethyl)phenyl]-1-propanol (165 mg, 49%) as a colorless solid.

Workup

  1. extractionlower, and then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-261c590a3f9c41f68d673d7b3cf6ef39
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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