Water → 5-Benzoyl-furan-2-carboxylic acid methyl ester

HRID 1900239Notes

Reaction equation

HRID 1900239 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([O:17][CH3:18])=[O:16].O>C(Cl)(Cl)(Cl)Cl>[C:2]1([C:1]([C:14]2[O:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 11902Methyl 2-furoate

Product 1

HCID 107757905-Benzoyl-furan-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Anhydrous ferric chloride 10.42 g, 0.0026 mole) and benzoyl chloride II-1(29.65 g, were dissolved in CCl4 (40 ml and added dropwise with methyl furan-2-carboxylate I-1 (24 g. 0.19 mole). The reaction mixture was then heated under refluxing for 16 hrs, and after cooling was added with water(120 ml). The mixture was extracted with CCl4 , then the CCl4 layer was washed with water, 5% sodium bicarbonate solution, and then with water, till neutral, then dried over anhydrous Magnesium sulfate and filtered. The solvent of the filtrate was evaporated under reduced pressure, the residue was recrystallized from isopropanol, and then from methanol to give compound V-1. Yield 18.75 g(42.9%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder refluxing for 16 hrs
  3. temperatureafter cooling
  4. extractionThe mixture was extracted with CCl4
  5. washthe CCl4 layer was washed with water, 5% sodium bicarbonate solution
  6. dry with materialwith water, till neutral, then dried over anhydrous Magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent of the filtrate was evaporated under reduced pressure
  9. customthe residue was recrystallized from isopropanol
  10. customfrom methanol to give compound V-1

Sources & evidence

ORD record
ord-6ff5d6a656b445d499e3a85545b7fd31
Source dataset
uspto-grants-1996_11
Patent number
US05574168

Reaction notes

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