Water → HCID 15908739, compound

HRID 1451511Notes

Reaction equation

HRID 1451511 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15](O)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12328546(2-Benzylphenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 15908739HCID 15908739, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-benzylphenylacetic acid (5.5 g, 24 mmol, J. Am. Chem. Soc. 1955, 77, 5078) in THF (100 ml) a solution of lithium aluminiumhydride in THF (24 ml, 24 mmol, 1M) was added dropwise on an ice-bath. When addition was complete the mixture was stirred for 1 h at ambient temperature. Water (1 ml), 4N sodium hydroxide (2 ml) and water (4 ml) were added successively. The mixture was filtered and the filtrate was diluted with diethylether (250 ml). The phases were separated and the organic phase was washed with saturated ammonium chloride solution (3×100 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 4.8 g of crude 2-(2-benzylphenyl)ethanol as an oil.

Workup

  1. additionWhen addition
  2. filtrationThe mixture was filtered
  3. additionthe filtrate was diluted with diethylether (250 ml)
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated ammonium chloride solution (3×100 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bdac4c3004664068b00b5728e4df5c56
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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