1-Bromohexane → 1,4-Dibromo-2,5-bis(hexyloxy)benzene

HRID 471360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471360
[OH-].[K+].[Br:3][C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Br:11])=[CH:6][C:5]=1[OH:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CS(C)=O>[Br:3][C:4]1[CH:9]=[C:8]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([Br:11])=[CH:6][C:5]=1[O:12][CH2:8][CH2:9][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

5

Edukt 3

HCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 2809452,5-Dibromohydroquinone

Produkt 1

HCID 167262041,4-Dibromo-2,5-bis(hexyloxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A suspension of KOH powder (10.47 g, 186.6 mmol) in dried DMSO (360 mL) was degassed under vigorous stirring for 1 h. 2,5-dibromo-1,4-dihydroxybenzene (5 g, 18.66 mol) and 1-bromohexane (5.8 mL, 41.06 mmol) were added and stirred for 12 h. The solution was concentrated and precipitated in water, filtered, washed with methanol. The product was recrystallized in ethanol, dried in vacuo (4.518 g, 55.5%). 1H NMR(300 MHz, CDCl3): δ 7.08 (s, 2H), 3.95 (t, 4H), 1.8 (m, 4H), 1.49 (m, 4H). 1.37 (m, 8H), 0.9 (t, 6H).

Aufarbeitung

  1. customwas degassed
  2. stirringstirred for 12 h
  3. concentrationThe solution was concentrated
  4. customprecipitated in water
  5. filtrationfiltered
  6. washwashed with methanol
  7. customThe product was recrystallized in ethanol
  8. customdried in vacuo (4.518 g, 55.5%)

Quellen und Nachweise

ORD-Eintrag
ord-ac65d9e1b72446fe9a359217dd2cf247
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633140B2

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