Acetyl chloride → Methyl 3-methyl-2-benzofurancarboxylate

HRID 1364588

Reaktionsgleichung

Reaktionsgleichung von HRID 1364588
[C:1](Cl)(=O)C.[CH3:5][C:6]1[C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[O:9][C:10]=1[C:11]([OH:13])=[O:12]>CO>[CH3:1][O:12][C:11]([C:10]1[O:9][C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[C:6]=1[CH3:5])=[O:13]

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 6005913-Methyl-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 74953Methyl 3-methyl-2-benzofurancarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Acetylchloride (6.7 mL, 91 mmol) was added dropwise to 750 mL dry methanol cooled on an ice-bath under N2 atmosphere. After completion of the addition, the solution was stirred at RT for 30 min. Subsequently, 16.0 g (90 mmol) 3-methyl benzo[b]furan-2-carboxylic acid was added and the solution was refluxed for 17 h under N2 atmosphere. The solution was cooled on an ice-bath to 0° C. and 500 mL ice-cold water was added. The resulting white precipitate was collected by filtration and washed with cold methanol. Yield: 16.1 g (94%) of a white solid. 1H-NMR (200 MHz, CDCl3): δ 7.72 (d, J=8 Hz, 1H), 7.60 (t, J=8 Hz, 1H), 7.53 (t, J=8 Hz, 1H), 7.41 (d, J=8 Hz, 1H), 4.08 (s, 3H), 2.73 (s, 3H) ppm.

Aufarbeitung

  1. temperaturecooled on an ice-bath under N2 atmosphere
  2. additionAfter completion of the addition
  3. temperaturethe solution was refluxed for 17 h under N2 atmosphere
  4. temperatureThe solution was cooled on an ice-bath to 0° C.
  5. filtrationThe resulting white precipitate was collected by filtration
  6. washwashed with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-ce658efffac144a1a633ef5e52c7aff9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888384B2

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