2'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acid → [2'-(Trifluoromethyl)[1,1'-biphenyl]-4-yl]methanol

HRID 1422335Notes

Reaction equation

HRID 1422335 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 27827142'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1394132[2'-(Trifluoromethyl)[1,1'-biphenyl]-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(2'-trifluoromethylphenyl)benzoic acid (1.525 g, 5.728 mmol) in THF (25 mL) at 0° C. was added 1.0 M lithium aluminum hydride in tetrahydrofuran (12.0 mL, 12.0 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 3 hours, cooled to 0° C., and quenched by dropwise addition of water (0.5 mL), 4 N aq. NaOH (0.5 mL), and water (1.5 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (Silica gel, 20% EtOAc in hexanes) to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.5 mL), 4 N aq. NaOH (0.5 mL), and water (1.5 mL)
  3. filtrationThe reaction was filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was chromatographed (Silica gel, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-07d6b03b541844a6a9d71e79e6297097
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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