p-Toluenesulfonic acid → 7-Methoxy-4,4-dimethylchromane

HRID 1350876Notes

Reaction equation

HRID 1350876 reaction equation
O[CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[OH:15])([CH3:6])[CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:9]=[C:8]2[C:7]([C:4]([CH3:5])([CH3:6])[CH2:3][CH2:2][O:15]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 210974522-(3-Hydroxy-1,1-dimethylpropyl)-5-methoxyphenol

Product 1

HCID 210975127-Methoxy-4,4-dimethylchromaneYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (30 ml) solution of 2-(3-hydroxy-1,1-dimethylpropyl)-5-methoxyphenol (3.0 g, 14.3 mmol) was added catalytic amount of p-toluenesulfonic acid. The stirred mixture was refluxed for 2 hours. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, 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=1/9 to furnish 2.1 g (75% yield) of the title compound as a colorless oil.

Workup

  1. temperatureThe stirred mixture was refluxed for 2 hours
  2. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate
  3. extractioncrude products were extracted with ethyl acetate The organic layer
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customto separate solvent and sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto give a residue, which
  10. washeluted with ethyl acetate/hexane=1/9

Sources & evidence

ORD record
ord-f83c78715ab3467384cebf3c553767fa
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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