4'-Trifluoromethyl-biphenyl-3-carboxylic acid → 4'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

HRID 2375728Notes

Reaction equation

HRID 2375728 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12](O)=[O:13])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[CH2:12][OH:13])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 27827184'-Trifluoromethyl-biphenyl-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanolYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Carboxylic acid 2.1 (13.3 g, 50 mmol) in anhydrous THF (100 mL) was added dropwise to LiAlH4 (2.9 g, 75 mmol) in anhydrous THF (150 mL) at 0° C. over 30 minutes. The resulting mixture was slowly warmed to room temperature and stirred for 4 hours. The reaction was slowly quenched with water (2.9 mL) at 0° C., 15% NaOH aqueous solution (2.9 mL) and another portion of water (8.7 mL). The mixture was dried over Na2SO4 and concentrated to give 2.2 as a white solid (11.9g).

Workup

  1. customThe reaction was slowly quenched with water (2.9 mL) at 0° C.
  2. dry with materialThe mixture was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c68a44861bf2457e930f9ee1fb2cbf04
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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