Aluminium lithium hydride → (2-Tert-butyl-5-aminophenyl)methanol

HRID 2189693Notes

Reaction equation

HRID 2189693 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:6]=1[C:7](OC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[C:1]([C:5]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:6]=1[CH2:7][OH:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57470263Methyl 2-tert-butyl-5-aminobenzoate

Product 1

HCID 57567299(2-Tert-butyl-5-aminophenyl)methanolYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-tert-butyl-5-aminobenzoate (159 mg, 0.72 mmol) in THF (5 mL) was added dropwise LiAlH4 (1.4 mL, 1M in THF, 1.4 mmol) at 0° C. The reaction mixture was refluxed for 2 h, diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. After filtration, the filtrate was concentrated to give (2-tert-butyl-5-aminophenyl)methanol (E-8) (25 mg, 20%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8.5 Hz, 1H), 6.87 (d, J=2.6 Hz, 1H), 6.56 (dd, J=8.4, 2.7 Hz, 1H), 4.83 (s, 2H), 1.36 (s, 9H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3ea775e53d434afd9fc3d52331ed06fa
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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