Water → (4'-Methylbiphenyl-2-yl)-methanol

HRID 1080821Notes

Reaction equation

HRID 1080821 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([C:20](O)=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1.C(OCC)(=O)C.O>O1CCCC1>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][OH:21])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 815682-(4-Methylphenyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1392422(4'-Methylbiphenyl-2-yl)-methanolYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooling suspension of lithium aluminium hydride (1.79 g) in tetrahydrofuran (50 ml) was added dropwise a solution of 4'-methylbiphenyl-2-carboxylic acid (5.0 g) in tetrahydrofuran (30 ml). The mixture was stirred for 17 hours at room temperature. To the reaction mixture were added ethyl acetate (10 ml) and water (50 ml), and insoluble materials were removed by filtration through celite. The filtrate was concentrated to dryness, and the residue was dissolved in ethyl acetate. The solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and dried. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel to afford the title compound as colorless syrup (3.95 g, 84%).

Workup

  1. customwere removed by filtration through celite
  2. concentrationThe filtrate was concentrated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c5020b0b7eb243e58091e28db4f36698
Source dataset
uspto-grants-1996_12
Patent number
US05583141

Reaction notes

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