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

HRID 1913765Notes

Reaction equation

HRID 1913765 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 aluminium 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 reaction is complete, saturated ammonium chloride solution is added to the mixture, which is taken up in ethyl acetate, and the organic phase is separated off and dried over sodium sulphate. 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 colourless solid are obtained.

Workup

  1. customAfter reaction
  2. customthe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. filtrationAfter filtration
  5. customthe solvent is removed in vacuo
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-ef6e18355bee42b1a89274964ea39518
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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