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

HRID 512638Notes

Reaction equation

HRID 512638 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-e1e4f2fc962b4afa858dce3d129ad703
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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