O-Cresol → 1-(2-Bromoethoxy)-2-methylbenzene

HRID 271228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271228
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].[Br:11][CH:12](Br)[CH3:13].S([O-])(O)(=O)=O.C([NH3+])(C)(C)C>>[Br:11][CH2:12][CH2:13][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Komponenten

5

Edukt 4

HCID 335O-CresolHCID 112011,1-DibromoethaneHCID 14798Sodium Hydroxide2×HCID 24996679t-Butylammonium hydrogen sulfate

Produkt 1

HCID 16225721-(2-Bromoethoxy)-2-methylbenzene

Versuchsvorschrift

2-Methyl-phenol (1 g, 9.25 mmol) in NaOH (aq) (3.24 mL, 12.96 mmol, 4M soln.) was treated with dibromoethane (2.74 mL, 31.7 mmol) and t-butylammoniumhydrogen sulfate (catalytic), and then placed in a Robbins™ oven at 99° C. for 72 hours. The pH was then adjusted to ˜8 with NaOH (4M aq. soln.) and the product extracted with CH2Cl2 (x3). The combined organic layer was washed with H2O (x2) and brine, dried over MgSO4. The resulting oil taken up in 4:1 hexane/EtOAc and passed through a plug of silica gel. The plug was then washed with 4:1 hexane/EtOAc and the filtrate concentrated to provide crude 2-bromo-1-(2-methylphenoxy)ethane.

Aufarbeitung

  1. extractionthe product extracted with CH2Cl2 (x3)
  2. washThe combined organic layer was washed with H2O (x2) and brine
  3. dry with materialdried over MgSO4
  4. washThe plug was then washed with 4:1 hexane/EtOAc
  5. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-21e6a719f0544b869f90d556cdfe0898
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452889B2

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