Toluene → 4-Acetoxypentanoic acid chloride

HRID 376166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376166
[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][C:8](O)=[O:9])(=[O:3])[CH3:2].C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:22])=O>CN(C)C=O>[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][C:8]([Cl:22])=[O:9])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 147371984-Acetoxypentanoic acid

Produkt 1

HCID 543443094-Acetoxypentanoic acid chlorideAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

46.5 g (0.29 mol) of 4-acetoxypentanoic acid are dissolved at room temperature in 230 ml of abs. toluene, and then 0.2 ml of abs. Dimethyl formamide is added. Then 32.6 ml (0.38 mol) of oxalyl chloride are added dropwise such that the evolution of gas remains under control. When the dropwise addition is complete, the reaction mixture is heated to 50° C. and stirred for 1 hour at this temperature. The orange-red reaction solution is concentrated by evaporation. Distillation of the residue gives 42.2 g of 4-acetoxypentanoic acid chloride as a colourless liquid of b.p.34 110°-112° C.

Aufarbeitung

  1. additionWhen the dropwise addition
  2. concentrationThe orange-red reaction solution is concentrated by evaporation
  3. distillationDistillation of the residue

Quellen und Nachweise

ORD-Eintrag
ord-f07c916ccf964837ade5afd1f6aa4503
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488140

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