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

HRID 1741722Notes

Reaction equation

HRID 1741722 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-ac8b8c425d5f42918929c332332773b7
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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