Diethyl Ether → 3-(Benzyloxy)-4-tert-butylphenol

HRID 1350882Notes

Reaction equation

HRID 1350882 reaction equation
C(OCC)C.C(=O)(OC(C)(C)C)[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH2:19]([O:18][C:10]1[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][C:11]=1[C:14]([CH3:16])([CH3:15])[CH3:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 210974783-(Benzyloxy)-4-tert-butylphenyl tert-butyl carbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 210974743-(Benzyloxy)-4-tert-butylphenolYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a diethylether (100 ml) solution of 3-(benzyloxy)-4-tert-butylphenyl tert-butyl carbonate (7.1 g, 20 mmol) was added lithium aluminum hydride (0.75 g, 20 mmol) at 0° C. The reaction mixture was 10 stirred at ambient temperature for 3 hours. To the mixture was added H2O (10 ml) carefully to form a white prepicitate. The organic layer was dried over magnesium sulfate. After filtration to separate solvent and magnesium sulfate and precipitate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane =1/6 to furnish 4.9 g (96% yield) of the title compound as colorless oil.

Workup

  1. customto form a white prepicitate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationAfter filtration
  4. customto separate solvent and magnesium sulfate and precipitate
  5. customthe solvent was removed under reduced pressure
  6. customto give a residue, which
  7. washeluted with ethyl acetate/hexane =1/6

Sources & evidence

ORD record
ord-a2188f2deb3f47d280944600596765fc
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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