2,4,6-Trichlorophenol → Bis(2,4,6-trichlorophenyl) benzylpropanedioate

HRID 928763

Reaktionsgleichung

Reaktionsgleichung von HRID 928763
[CH2:1]([CH:8]([C:12]([OH:14])=[O:13])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1O.O=P(Cl)(Cl)Cl>>[CH2:1]([CH:8]([C:9]([O:11][C:17]1[C:16]([Cl:15])=[CH:21][C:20]([Cl:22])=[CH:19][C:18]=1[Cl:23])=[O:10])[C:12]([O:14][C:21]1[C:16]([Cl:15])=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=1[Cl:22])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 69142,4,6-TrichlorophenolHCID 12031Benzylmalonic acidHCID 24813Phosphorus oxychloride

Produkt 1

HCID 2782299Bis(2,4,6-trichlorophenyl) benzylpropanedioate

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 2-benzylmalonic acid (10.0 g, 51.5 mmol), 2,4,6-trichlorophenol (20.3 g, 103 mmol), and POCl3 (12.0 mL, 129 mmol) was stirred under air at 105° C. for 2 hours. The reaction was then cooled to room temperature, poured on 150 mL ice, and extracted with 4:1 ether/DCM (3×150 mL). The combined organic layers were washed with water (1×400 mL) and 4 M aqueous NaCl (1×100 mL), and the yellow organic layer was dried (Na2SO4), filtered, and concentrated by rotary evaporation at <40° C. to provide the title compound as a tan thick oil that became a beige solid upon standing.

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with 4:1 ether/DCM (3×150 mL)
  3. washThe combined organic layers were washed with water (1×400 mL) and 4 M aqueous NaCl (1×100 mL)
  4. dry with materialthe yellow organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation at <40° C.

Quellen und Nachweise

ORD-Eintrag
ord-65d5e616cc48453390f5f22d30d5e56a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290476B2

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