Potassium Iodide → Ethyl 3,5-dimethyl-4-(3-ethynylpropoxy)benzoate

HRID 1681921

Reaktionsgleichung

Reaktionsgleichung von HRID 1681921
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:14])[C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[I-].[K+].Cl[CH2:18][CH2:19][CH2:20][C:21]#[CH:22].[OH-].[K+]>C(#N)C>[CH3:14][C:11]1[CH:10]=[C:4]([CH:3]=[C:2]([CH3:1])[C:12]=1[O:13][CH2:22][CH2:21][CH2:20][C:19]#[CH:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 843081-Pentyne, 5-chloro-HCID 3027494Ethyl 3,5-dimethyl-4-hydroxybenzoate

Produkt 1

HCID 15057290Ethyl 3,5-dimethyl-4-(3-ethynylpropoxy)benzoateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 6.42 g ethyl 3,5-dimethyl-4-hydroxybenzoate, 5.5 g potassium iodide, 3.7 g 1-chloro-4-pentyne and 2.3 g powdered potassium hydroxide in 650 ml acetonitrile was heated at reflux under nitrogen for 16 hrs. The mixture was filtered, concentrated in vacuo and subjected to flash filtration (silica gel, 4:1 hexane/ethyl acetate) to give 7.4 g ethyl 3,5-dimethyl-4-(3-ethynylpropoxy)benzoate as a yellow oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 16 hrs
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. filtrationsubjected to flash filtration (silica gel, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9796020021f64d6cba3189ebc17902fe
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175178

Verknüpfte Notizen

Wird geladen…