Ethanol → Diethyl 2,2'-(1,3-phenylene)diacetate

HRID 1985981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985981
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=[O:9])[CH:2]=1.[C:15](Cl)(=O)[CH3:16].[CH2:19](O)[CH3:20]>>[CH2:19]([O:9][C:8](=[O:10])[CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1)[CH3:20]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 29788m-Phenylenediacetic acid

Produkt 1

HCID 19863769Diethyl 2,2'-(1,3-phenylene)diacetate

Versuchsvorschrift

2,2′-(1,3-Phenylene)diacetic acid (10.0 g, 51 mmol) was dissolved in ethanol (100 mL) and the solution treated dropwise with acetyl chloride (2.5 mL). The reaction mixture was stirred at reflux for 18 hours before being allowed to cool and concentrated in vacuo. The residue was taken up in ethyl acetate (100 mL) and extracted with sodium bicarbonate solution (3×50 mL) and brine (3×50 mL). The organic phase was dried (MgSO4), concentrated in vacuo and the residue triturated with pentane to yield the product (11.8 g). 1HNMR (CDCl3, 400 MHz) δ: 1.31 (6H, t), 3.65 (4H, s), 4.20 (4H, q) 7.24-7.36 (4H, m); LRMS ESI m/z 251 [M+H]+

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. extractionextracted with sodium bicarbonate solution (3×50 mL) and brine (3×50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue triturated with pentane

Quellen und Nachweise

ORD-Eintrag
ord-e9a79e9deffa490ea1e057af2fa85dde
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547731B2

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