Hydrochloric Acid → 4-Hydroxy-3-[2-(4-methylphenyl)ethyl]benzofuran

HRID 230872Notes

Reaction equation

HRID 230872 reaction equation
[OH:1][C:2]1[C:7]([C:8](=O)[CH:9]=[CH:10][CH:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH2:12]2)=[C:6]([O:19][CH2:20]C(OC)=O)[CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO>[OH:1][C:2]1[C:7]2[C:8]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[CH:20][O:19][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 671360496'-Hydroxy-2'-methoxycarbonylmethoxy-4-methyldihydrochalcone

Product 1

HCID 231035724-Hydroxy-3-[2-(4-methylphenyl)ethyl]benzofuranYield 29.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6′-hydroxy-2′-methoxycarbonylmethoxy-4-methyldihydrochalcone (0.58 g) in methanol (10 mL) was added sodium methoxide (28% methanol solution, 0.68 mL), and the mixture was heated for reflux overnight. The reaction mixture was cooled to room temperature and poured into 1 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (0.13 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturefor reflux overnight
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-45381cca27e14a78ae6f16510cbbc7a6
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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