Water → HCID 66904792, compound

HRID 1690197Notes

Reaction equation

HRID 1690197 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[OH:13])[CH:2]=[CH2:3].O>C(Cl)Cl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH3:3][CH:2]1[CH2:1][C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=2[O:13]1

Participants

5

Reactant 2

HCID 962WaterHCID 66904884HCID 66904884, compound

Product 1

HCID 66904792HCID 66904792, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4-Allyl-3-hydroxyphenyl)ethanone (863 mg, 4.90 mmol) was dissolved in methylene chloride (25 mL), which was then added with zirconium (IV) chloride (1.37 g, 5.88 mmol) at room temperature under an argon atmosphere, and stirred overnight. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (n-hexane/ethyl acetate=6/1). 1-(2-Methyl-2,3-dihydrobenzofuran-6-yl)ethanone (167 mg, yield 19%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-ba64c2b4c829485ba41a4946e175e8c9
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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