Hydrochloric Acid → 3-(furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one

HRID 2362222Notes

Reaction equation

HRID 2362222 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.C[O-].[Na+].Cl>CO>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=[CH:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 74764'-MethoxyacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 2440833-(furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-oneYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-(4-methoxyphenyl)ethanone (17.0 g, 113.0 mmol) in methanol (240 mL) was added a solution of 2-furaldehyde (12.0 g, 125.0 mmol) in methanol (240 mL) followed by the addition of sodium methoxide (6.10 g, 113.0 mmol). The reaction mixture was stirred at room temperature for 24 h, and then was neutralized with HCl aq. (6.0 M, 18.8 mL). The volatile was removed in vacuum. The residue was dissolved in ethyl acetate (500 mL), washed with water (250 mL) and brine (250 mL), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=5:1˜3:1) to afford 3-(furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (25B) as a yellow solid (23.80 g, 92%).

Workup

  1. customThe volatile was removed in vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  3. washwashed with water (250 mL) and brine (250 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (PE:EA=5:1˜3:1)

Sources & evidence

ORD record
ord-1c47cd3d76294665b021ecc6007e7011
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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