Reaktion #41210

ord-3460ff4893ad4905a99f8400ac94a8e1

Reaktionsgleichung

CCC#CBr
butynyl bromide
Oc1ccc(O)cc1
hydroquinone
O=C([O-])[O-].[K+].[K+]
K2CO3
CC#CCOc1ccc(O)cc1
crude product
Ausbeute 25.0%
CC#CCOc1ccc(O)cc1
4-But-2-ynyloxy-phenol
Ausbeute 25.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas refluxed for 10 h
  2. 2
    SonstigeSolvent was removed in vacuo
  3. 3
    workup.DISSOLUTIONthe crude product was dissolved in EtOAc
  4. 4
    Sonstigepartitioned with water
  5. 5
    SonstigeOrganic layer was separated
  6. 6
    Waschenwashed with water
  7. 7
    Trocknendried over anhydrous Na2SO4
  8. 8
    SonstigeThe solvent was removed in vacuo

Vorschrift

To a solution containing butynyl bromide (1 g, 7.5 mmol), hydroquinone (827 mg, 7.5 mmol), and K2CO3 (1.04 g, 7.5 mmol) was refluxed for 10 h. Solvent was removed in vacuo and the crude product was dissolved in EtOAc and partitioned with water. Organic layer was separated and washed with water and dried over anhydrous Na2SO4. The solvent was removed in vacuo to obtain the crude product (0.3 g, 25%), which was used for the next step without further purification; LCMS 99%, m/z 162.2 (M+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728032B2uspto-grants-2010_06