Water → (4'-Methoxy[1,1'-biphenyl]-4-yl)methanol

HRID 1072703Notes

Reaction equation

HRID 1072703 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1393415Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1051637(4'-Methoxy[1,1'-biphenyl]-4-yl)methanolYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-(4′-methoxyphenyl)benzoate (3.0 g, 12.3 mmol) was added in portions to a suspension of lithium aluminum hydride (0.94 g, 25.0 mmol) in tetrahydrofuran (40 ml) at room temperature for 20 minutes with stirring. The reaction solution was refluxed for 2 hours under heating and cooled to 0° C. To the residue was added water (1 ml) and 1 N aqueous sodium hydroxide (3 ml), the insoluble matter was filtered out and the filtrate was concentrated under reduced pressure. The object compound (1.2 g) was obtained from the residue as colorless crystals.

Workup

  1. temperatureThe reaction solution was refluxed for 2 hours
  2. temperatureunder heating
  3. filtrationthe insoluble matter was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d216088228f4668997d23a1dc2d4284
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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