Phthalic Anhydride → 2-(2-Thienylcarbonyl)benzoic acid

HRID 628205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628205
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:15])[O:10][C:8](=[O:9])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[S:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>ClCCl>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:8]([C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[C:5]([OH:10])=[O:15])=[O:9]

Komponenten

5

Edukt 3

HCID 6811Phthalic AnhydrideHCID 8030ThiopheneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2826542-(2-Thienylcarbonyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Aluminum chloride (58.7 g, 440 mmol, 2.2 equiv.) and dichloromethane (150 mL) were added to a round bottom flask. A solution of phthalic anhydride (29.6 g, 200 mmol, 1.0 equiv.) in dichloromethane (150 mL) was then added, and the mixture was stirred at room temperature for 30 minutes. Thiophene (15.8 mL, 200 mL, 1.0 equiv.) was added over 1 hour, after which the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was cautiously quenched with hydrochloric acid (0.2 M, 1 L), extracted with dichloromethane, and extracted with aqueous NaOH (1 N, 3×200 mL). The aqueous layer was acidified with concentrated hydrochloric acid; the solids were collected by filtration, and stirred in refluxing methanol. The suspension was filtered, and water was added to the filtrate to crystallize 1 as a colorless solid (20.7 g, 45%). 1H NMR (500 MHz, CDCl3) δ8.09 (dd, J=7.8, 0.85 Hz, 1H), 7.70 (dd, J=4.9, 1.1 Hz, 1H), 7.67 (td, J=7.5, 1.3 Hz, 1H), 7.58 (td, J=7.8, 1.3 Hz, 1H), 7.47 (dd, J=7.5, 0.90, 1H), 7.27-7.26 (m, 1H), 7.07-7.06 (m, 1H). m.p 144-145° C.

Aufarbeitung

  1. stirringafter which the reaction mixture was stirred for 3 hours at room temperature
  2. customThe reaction mixture was cautiously quenched with hydrochloric acid (0.2 M, 1 L)
  3. extractionextracted with dichloromethane
  4. extractionextracted with aqueous NaOH (1 N, 3×200 mL)
  5. filtrationthe solids were collected by filtration
  6. stirringstirred
  7. temperaturein refluxing methanol
  8. filtrationThe suspension was filtered
  9. additionwater was added to the filtrate
  10. customto crystallize 1 as a colorless solid (20.7 g, 45%)
  11. customm.p 144-145° C.

Quellen und Nachweise

ORD-Eintrag
ord-53ae5e94bf874d3cac512981bf01d3f8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09312501B2

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