Benzoyl chloride → 4-(Furan-2-yl)-2,6-dimethoxyphenyl benzoate

HRID 56539Notes

Reaction equation

HRID 56539 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=1.CCN(CC)CC.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:24]([O:14][C:9]1[C:8]([O:15][CH3:16])=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:11][C:10]=1[O:12][CH3:13])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 543508354-(Furan-2-yl)-2,6-dimethoxyphenol

Product 1

HCID 584319964-(Furan-2-yl)-2,6-dimethoxyphenyl benzoateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(furan-2-yl)-2,6-dimethoxyphenol (1.3 g, 5.9 mmol) in anhydr CH2Cl2 (20 mL) under argon was added Et3N (1.6 mL, 11.5 mmol) then the mixture was cooled over an ice bath. Benzoyl chloride (0.75 mL, 6.4 mmol) was added dropwise and the reaction was stirred for 3 hrs. 10% aqueous NaHCO3 and CH2Cl2 were added, stirred, and the layers were separated. The organics were washed with H2O and saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. Purification by chromatography (0-25% EtOAc-hexanes) gave 4-(furan-2-yl)-2,6-dimethoxyphenyl benzoate as a light yellow solid (0.54 g isolated from chromatography of approximately half of the crude product; 57% yield).

Workup

  1. temperaturethe mixture was cooled over an ice bath
  2. stirringstirred
  3. customthe layers were separated
  4. washThe organics were washed with H2O and saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (0-25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-5add161b8f0e4ac89eb3c1944c095e46
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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