Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(3-formylphenyl)acetamide

HRID 852881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852881
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[CH:2]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1)=[O:1]

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 13987600N-[3-(1,3-dioxolan-2-yl)phenyl]acetamide

Produkt 1

HCID 256849N-(3-formylphenyl)acetamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18366337Propan-2-one--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of N-(3-[1,3]Dioxolan-2-yl-phenyl)-acetamide (7.8 g, 0.037 mol) and pyridinium-p-toluenesulfonate (2.8 g, 0.011 mol) in acetone-water (4:1, 400 mL) was refluxed for 1 hr. The solution was then cooled to room temperature, and the bulk of the solvent (˜90%) removed under reduced pressure. The remaining solution was then extracted with EtOAc, and the combined extracts washed with saturated NaHCO3, brine, and dried with MgSO4. Evaporation of the solvent gave N-(3-Formyl-phenyl)-acetamide (5.98 g, 98%) as an orange oil. 1H NMR (CDCl3) δ 2.22 (s, 3H), 7.46 (t, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 8.07 (s, 1H), 8.69 (br s, 1H), 9.94 (s, 1H). 13C NMR (CDCl3) δ 193.9, 171.0, 140.8, 138.5, 131.2, 127.5, 127.1, 122.0, 26.0.

Aufarbeitung

  1. temperaturewas refluxed for 1 hr
  2. customthe bulk of the solvent (˜90%) removed under reduced pressure
  3. extractionThe remaining solution was then extracted with EtOAc
  4. washthe combined extracts washed with saturated NaHCO3, brine
  5. dry with materialdried with MgSO4
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-ee0052e72b4449dd90637151a0802cf1
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253194B2

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