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Water → 2-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene

HRID 219050
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 219050
[OH-].[Na+].[Cl:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:5]=1[CH2:6][O:7][CH2:8][CH2:9][OH:10].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:10][CH2:9][CH2:8][O:7][CH2:6][C:5]1[C:4]([Cl:3])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 13341669Ethanol, 2-((2,6-dichlorophenyl)methoxy)-

Produkt 1

HCID 668449032-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzeneAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236
Tetrabutylammonium Bromide
Katalysator
HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

50% aq NaOH (1.89 L), 2-(2,6-dichlorobenzyloxy)ethanol (473.2 g), 1,6-dibromohexane (2.44 kg, 5eq) and tetrabutylammonium bromide (34.1 g, 5 mol %) in toluene (1.89 L) was heated to 55-60° C. for 8-20 h. On cooling water (558 mL) and toluene (558 mL) were added. The aqueous phase was separated and diluted with water (1 L) then back extracted with toluene (1.1 L). The combined toluene extracts were washed twice with water (2.2 L), then evaporated to dryness on a rotary evaporator. The excess 1,6-dibromohexane was removed using a wiped film evaporator, and the resulting crude product chromatographed on silica (5 kg Biotage), eluting with 5% ethyl acetate in petrol 60/80, to give the title compound (503.2 g)—LC RT=7.0 min.

Aufarbeitung

  1. additionwere added
  2. customThe aqueous phase was separated
  3. additiondiluted with water (1 L)
  4. extractionthen back extracted with toluene (1.1 L)
  5. washThe combined toluene extracts were washed twice with water (2.2 L)
  6. customevaporated to dryness on a rotary evaporator
  7. customThe excess 1,6-dibromohexane was removed
  8. customa wiped film evaporator
  9. customthe resulting crude product chromatographed on silica (5 kg Biotage)
  10. washeluting with 5% ethyl acetate in petrol 60/80

Quellen und Nachweise

ORD-Eintrag
ord-c27e97d533db48f29b8bb76197b9ff57
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198483B2

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