beta-Phenylisovaleric acid → 3-Methyl-3-phenylbutan-1-ol

HRID 704414Notes

Reaction equation

HRID 704414 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4](O)=[O:5].[Li].[H-].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:1])[CH2:3][CH2:4][OH:5]

Participants

6

Reactant 4

HCID 13890beta-Phenylisovaleric acidHCID 166653HydrideHCID 516892Sodium BicarbonateHCID 3028194Lithium

Product 1

HCID 2324603-Methyl-3-phenylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-3-phenylbutanoic acid (0.90 9) was dropwise added to a suspension of lithium alminum hydride (0.2 g) in 15 ml of tetrahydrofuran at room temperature and the mixture was stirred for 30 minutes. To the reaction mixture was added a saturated aqueous solution of sodium bicarbonate under ice cooling, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride,, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (20 g). Elution with a hexane ethyl acetate (5:1) mixture gave 0.75 g of 3-metyl-3-phenylbutanol.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washElution with a hexane ethyl acetate (5:1) mixture

Sources & evidence

ORD record
ord-f44441e6c92241f4803cf0b43b831589
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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