Ammonium Chloride → (4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

HRID 1927416Notes

Reaction equation

HRID 1927416 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:27])([F:26])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](OCC)=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:7][C:8]([F:26])([F:27])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 547624251,1'-Biphenyl-4-carboxylic acid,4'-(trifluoromethyl)-,ethyl ester

Product 1

HCID 22015014(4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

12.73 ml (12.73 mmol) of a 1 M solution of lithium aluminum hydride in THF are added dropwise to a solution of 6.24 g (21.21 mmol) of ethyl 4′-trifluoromethylbiphenyl-4-carboxylate in 60 ml of dry THF at 0° C. After the reaction is complete, the mixture is mixed with saturated ammonium chloride solution and taken up in ethyl acetate, and the organic phase is separated off and dried over sodium sulfate. After filtration, the solvent is removed in vacuo. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). 5.1 g (20.21 mmol, 95% of theory) of a colorless solid are obtained.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent is removed in vacuo
  5. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1)
  6. custom5.1 g (20.21 mmol, 95% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-16e6ea95f84f4de2af47d931b39655a7
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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