Tetrahydrofuran → 2-(3-Hydroxy-1,1-dimethylpropyl)-5-methoxyphenol

HRID 1350875Notes

Reaction equation

HRID 1350875 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:20])([CH3:19])[CH2:13][C:14](=[O:18])[O:15]2)=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:18][CH2:14][CH2:13][C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:17][C:16]=1[OH:15])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 210975117-Methoxy-4,4-dimethylchroman-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 210974522-(3-Hydroxy-1,1-dimethylpropyl)-5-methoxyphenolYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydorofran (THF) (20 ml) solution of 7-methoxy-4,4-dimethylchroman-2-one (4.1 g, 19.7 mmol) was added lithium aluminum hydride (750 mg, 19.7 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. To the mixture was added H2O (1 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=¼ to furnish 3.0 g (76% 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=¼

Sources & evidence

ORD record
ord-bd52f443d3304e009209d9a50e222624
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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