Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-3-methylbutyrate

HRID 279912

Reaktionsgleichung

Reaktionsgleichung von HRID 279912
[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][CH:19]1[CH2:25][C:24](=[O:26])[O:23][C:21](=[O:22])[CH2:20]1.C(N(CC)CC)C>CCOCC>[C:21]([CH2:20][CH:19]([CH3:18])[CH2:25][C:24]([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:26])([OH:23])=[O:22]

Komponenten

5

Edukt 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 778283-Methylglutaric anhydride

Produkt 1

HCID 233228965-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-3-methylbutyrateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of triclosan (22.3 g.), 3-methylglutaric anhydride (15.0 g.) and triethylamine (15 ml.) in ether (250 ml.) was stirred for 20 hours, and then washed first with 2M hydrochloric acid (50 ml.) and then with water (3×150 ml.). The ether phase was dried (MgSO4) and evaporated. A portion (20 g.) of the residual oil was purified by chromatography on silica gel using methylene chloride as eluant to give (D) as a colourless oil (7.4 g.) ; NMR (CDCl3): 0.8-1.3 (3H,d, CH3), 2.1-2.8 (5H,m,CH2CO+CH3CH), 6.7-7.6 (6H, m, aromatic H), 11.25 (1H,s, CO2H)ppm.

Aufarbeitung

  1. washwashed first with 2M hydrochloric acid (50 ml.)
  2. dry with materialThe ether phase was dried (MgSO4)
  3. customevaporated
  4. customA portion (20 g.) of the residual oil was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9c22268e69f445f58f3de5e07ed5e4a6
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587262

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