Ethylene Glycol → 5,7-Di-tert-butyl-1,4-benzodioxine

HRID 330717

Reaktionsgleichung

Reaktionsgleichung von HRID 330717
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1O)[OH:8])([CH3:4])([CH3:3])[CH3:2].BrCCBr.C(=O)([O-])[O-].[K+].[K+].[CH2:27](O)[CH2:28][OH:29]>O>[C:1]([C:5]1[C:6]2[O:29][CH:28]=[CH:27][O:8][C:7]=2[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 755502,6-Di-tert-butylhydroquinone

Produkt 1

HCID 138379325,7-Di-tert-butyl-1,4-benzodioxine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3,5-Di-tert-butylhydroquinone (3.33 g, 15 mmol) was combined with 1,2-dibromoethane (5.6 g), potassium carbonate (4.35 g) and ethylene glycol (25 mL). The mixture was heated in a 120° C. oil bath under an Ar atmosphere for 12 h. Water was added to the reaction mixture to quench the reaction and then the organic compound was extracted by CH2Cl2. The resulting solution was concentrated to afford a crude oil. The crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture to afford the title compound (Rf=0.5, 5:1 hexane/ethyl acetate). 1H NMR (500 MHz, CDCl3): δ 7.03 (d, J=2 Hz, 1H), 6.93 (d, J=2 Hz, 1H), 4.34 (s, 4H), 1.53 (s, 9H), 1.43 (s, 9H).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe organic compound was extracted by CH2Cl2
  4. concentrationThe resulting solution was concentrated
  5. customto afford a crude oil
  6. customThe crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture

Quellen und Nachweise

ORD-Eintrag
ord-c247f44ca28e4ae882317b74efb8bdc6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877390B2

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