Ethanol → Ethyl 2,4-dimethylbenzoate

HRID 1907038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907038
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[OH-].[Ca+2].[OH-].[CH2:20](O)[CH3:21]>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH3:21])=[O:5]

Komponenten

5

Edukt 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 118972,4-Dimethylbenzoic acidHCID 6093208Calcium Hydroxide

Produkt 1

HCID 118492Ethyl 2,4-dimethylbenzoateAusbeute 95 %

Versuchsvorschrift

To a solution of commercially available 2,4-dimethylbenzoic acid (67.8 g, 451 mmol) in 1000 mL of ethanol was added 10 mL of sulfuric acid. The mixture was refluxed over night, cooled down and was neutralized by adding calcium hydroxide in small portions (˜30 g). The suspension was filtered over celite and concentrated in vacuo. The crude product was purified by vacuum distillation yielding 76.4 g (95%) of 1 as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 1.38 (t, J=7.3 Hz, 3H), 2.34 (s, 3H), 2.57 (s, 3H), 4.33 (q, J=7.2 Hz, 2H), 7.01-7.06 (m, 2H), 7.82 (d, J=8.5 Hz, 1H); 13C-NMR (100 MHz, CDCl3): δ 14.3, 21.3, 21.7, 60.4, 126.3, 126.9, 130.7, 132.4, 140.1, 142.3, 167.6; MS (ESI) m/z=133.0 (100), 132.0 (57), 178.1 (M+, 51).

Aufarbeitung

  1. temperatureThe mixture was refluxed over night
  2. temperaturecooled down
  3. filtrationThe suspension was filtered over celite and
  4. concentrationconcentrated in vacuo
  5. distillationThe crude product was purified by vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-2be7d153eea24d71a5c612c88a56299c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08597631B2

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