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

HRID 1806864Notes

Reaction equation

HRID 1806864 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].B.C1COCC1>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

4

Reactant 2

HCID 13890beta-Phenylisovaleric acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 2324603-Methyl-3-phenylbutan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Step A To a solution of 3-methyl-3-phenylbutanoic acid (ChemBridge) (4.46 g, 25 mmol) in anhydrous tetrahydrofuran (150 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of BH3.THF (Aldrich, 50 mL, 50 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 3 h, then concentrated. The residue was partitioned between ethyl acetate and water. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3-methyl-3-phenyl-butan-1-ol as a colorless oil (4.1 g, 100%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe organic layer were separated
  4. washwashed with water, aqueous HCl solution, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-869db1525e3f49b08d3e50649ad39717
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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