Bromobenzene → 1-Pentadecyl-3-phenoxybenzene

HRID 2276625

Reaktionsgleichung

[K].[CH2:2]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(N(C)C)=O>O>[CH2:2]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

Into a 1000 mL round bottom flask containing potassium salt of 3-pentadecyl phenol (111.0 g, 0.32 mol) was added bromobenzene (50.88 g, 0.32 mol) followed by Cu powder (2.22 g, 2 wt %) and DMAc (150 mL). The reaction mixture was heated at 150° C. for 6 h. After completion of the reaction, the obtained dark colored reaction mixture was poured into water (500 mL); the Cu salts were removed by filtration. The filtrate was extracted with ethyl acetate (2×300 mL), washed with saturated aqueous sodium chloride solution (2×100 mL) followed by water (3×100 mL) and dried over sodium sulfate. Solvent evaporation yielded crude 1-pentadecyl-3-phenoxybenzene. Pure 1-pentadecyl-3-phenoxybenzene was obtained after silica gel (60-120 mesh) column chromatography (eluent: pet ether). Yield 70 g (57%); MP 32° C.

Aufarbeitung

customAfter completion of the reaction
customthe Cu salts were removed by filtration
extractionThe filtrate was extracted with ethyl acetate (2×300 mL)
washwashed with saturated aqueous sodium chloride solution (2×100 mL)
dry with materialdried over sodium sulfate
customSolvent evaporation
customyielded crude 1-pentadecyl-3-phenoxybenzene

Quellen und Nachweise

ORD-Eintrag: ord-5391f8dc50de4030afccdb7d6a4970b7
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09133089B2

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