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Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl prop-2-enoate

HRID 991379
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 991379
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]([OH:8])=[C:3]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[CH:2]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27]>O1CCCC1>[CH2:27]=[CH:26][C:25]([O:8][C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])=[O:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 13140Acryloyl chloride2×

Produkt 1

HCID 673466385-Chloro-2-(2,4-dichlorophenoxy)phenyl prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Irgasan® DP300 5-chloro-2-(2,4-dichlorophenol)(triclosan), 23.5 g (0.081 mol) was dissolved in 300 ml of dry tetrahydrofuran in a 1-l jacketed kettle with agitator, addition funnel and reflux condenser. Then 10.6 ml of triethylamine was added to the solution with agitation. To the resulting solution was added dropwise 6.68 (0.0738 mol) g of acryloyl chloride. The reaction temperature was maintained at 20° C. with a circulating cooling bath. After the addition of acryloyl chloride was completed, the agitation and temperature conditions were maintained for 5 hours. Then the reaction product was kept overnight at room temperature, filtered to remove solid triethylamine hydrochloride and the filtrate rotovapped at room temperature under 100-110 mm Hg to concentrate the product. The remaining solution was dissolved in 100 ml heptane and washed with 5% Na2CO3 solution in Dl water until basic; then with Dl water until neutral. The heptane solution of the product was dried with MgSO4 in a refrigerator overnight, and filtered. The filtrate contained 25.3% triclosan acrylate as determined by bromination. FTIR spectrum confirmed the presence of the unsaturated ester of a phenol (1753 cm−1).

Aufarbeitung

  1. temperaturereflux condenser
  2. temperaturea circulating cooling bath
  3. temperaturethe agitation and temperature conditions were maintained for 5 hours
  4. filtrationfiltered
  5. customto remove solid triethylamine hydrochloride
  6. customrotovapped at room temperature under 100-110 mm Hg
  7. concentrationto concentrate the product
  8. dissolutionThe remaining solution was dissolved in 100 ml heptane
  9. washwashed with 5% Na2CO3 solution in Dl water until basic
  10. dry with materialThe heptane solution of the product was dried with MgSO4 in a refrigerator overnight
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-541733ca58234a7d962701877abd65d5
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06464961B2

Notizen zur Reaktion

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