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

HRID 1672623Notes

Reaction equation

HRID 1672623 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)methanolYield 95.3%

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 from Example 21A 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% yield) 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)

Sources & evidence

ORD record
ord-dcd5b1d49ade4da887c0b2a2d031dcb8
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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