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

HRID 1921870Notes

Reaction equation

HRID 1921870 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

12.7 ml (12.7 mmol) of a 1 M lithium aluminum hydride solution in THF are slowly added to a solution of 6.24 g (21.2 mmol) of ethyl 4′-trifluoromethylbiphenyl-4-carboxylate in 60 ml of dry THF at 0° C. After the reaction is complete, the mixture is hydrolyzed 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 60 (mobile phase: cyclohexane/ethyl acetate 5:1). 5.10 g (20.2 mmol, 95% of theory) of the title compound 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 60 (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-e9fcdf766497464fbd7dcffcb1355419
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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