Hydrochloric Acid → [4-(4-Fluorophenyl)phenyl]methanol

HRID 257066Notes

Reaction equation

HRID 257066 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.Cl>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1394448Methyl 4'-fluoro-1,1'-biphenyl-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1394497[4-(4-Fluorophenyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.86 g, 74.4 mmol) in THF (300 ml) at 0°, is added methyl 4'-fluoro-4-biphenylyl-carboxylate (8.67 g, 37.7 mmol) as a solution in THF (100 ml). The resulting mixture is stirred for 1 hour and subsequently allowed to warm to room temperature. The reaction mixture is chilled to 0° and 2N HCl (100 ml) is slowly added. The resulting mixture then is extracted with Et2O (2×150 ml). The combined organic portions are washed with saturated NaHCO3 solution (400 ml), saturated NaCl solution (400 ml), dried over MgSO4 and concentrated in vacuo, to yield 4'-fluoro-4-biphenylyl-methanol as a white solid.

Workup

  1. temperatureThe reaction mixture is chilled to 0°
  2. extractionThe resulting mixture then is extracted with Et2O (2×150 ml)
  3. washThe combined organic portions are washed with saturated NaHCO3 solution (400 ml), saturated NaCl solution (400 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d84f3e16e15b480d888d7482222552a3
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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