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Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate

HRID 279911
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 279911
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]([OH:8])=[C:3]([O:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])[CH:2]=1.[CH3:18][C:19]1([CH3:27])[CH2:25][CH2:24][C:23](=[O:26])[O:22][C:20]1=[O:21]>C(N(CC)CC)C>[C:23]([CH2:24][CH2:25][C:19]([CH3:27])([CH3:18])[C:20]([O:8][C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=1[Cl:16])=[O:21])([OH:26])=[O:22]
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Komponenten

4

Edukt 2

HCID 5564TriclosanHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

Produkt 1

HCID 233229055-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of triclosan (29.0 g.), triethylamine (15 ml.) and 2,2-dimethylglutaric anhydride (20 g.) was heated at 80° C. for 5 hours. A further quantity (2.0 g.) of anhydride and triethylamine (1 ml.) were added and heating continued for 24 hours. The mixture was cooled to ambient temperature, washed with 2M hydrochloric acid (100 ml.), then with water (3×80 ml.) and dried (MgSO4). The solution obtained was evaporated. The brown residual oil was dissolved in hot cyclohexane. The solution on cooling gave white crystals which were recrystallised from cyclohexane/petrol 60-80 to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate (C') (12.7 g.), m.p. 125°-128° C.

Aufarbeitung

  1. temperatureheating
  2. temperatureThe mixture was cooled to ambient temperature
  3. washwashed with 2M hydrochloric acid (100 ml.)
  4. dry with materialwith water (3×80 ml.) and dried (MgSO4)
  5. customThe solution obtained
  6. customwas evaporated
  7. dissolutionThe brown residual oil was dissolved in hot cyclohexane
  8. temperatureThe solution on cooling
  9. customgave white crystals which
  10. customwere recrystallised from cyclohexane/petrol 60-80

Quellen und Nachweise

ORD-Eintrag
ord-d097fe9abe56492db156157af1bcf77c
Quelldatensatz
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04587262

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