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

HRID 2225018Notes

Reaction equation

HRID 2225018 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 esterYield 61,681.199%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Anhydrous ferric chloride (0.42 g, 2.6 mmole) and benzoyl chloride (29.6 g, 0.21 mole), were dissolved in CCl4 (40 ml) and added dropwise over 10 min with methyl 2-furoate (25.2 g, 0.20 mmole). The reaction mixture was then heated under reflux for 36 hrs, and after cooling was added with water (120 ml). The mixture was stirred for 1 hr and then allowed to sit until it separated into two layers. The water layer and precipitate were extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The solvent of the filtrate was removed under a reduced pressure; the residue was recrystallized from isopropanol to afford 28.4 g 5-methoxycarbonyl-2-furyl phenyl ketone in a yield of 65.0%.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 36 hrs
  3. temperatureafter cooling
  4. customseparated into two layers
  5. extractionThe water layer and precipitate were extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent of the filtrate was removed under a reduced pressure
  9. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-78697624a79a4a2684fd81cffdad789b
Source dataset
uspto-grants-2008_05
Patent number
US07378532B2

Reaction notes

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