Benzyl Bromide → 2-Benzyloxy-1-methyl-4-nitro-benzene

HRID 427608

Reaktionsgleichung

Reaktionsgleichung von HRID 427608
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 935762-Methyl-5-nitrophenol

Produkt 1

HCID 181745022-Benzyloxy-1-methyl-4-nitro-benzeneAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2-methyl-5-nitrophenol (2.0 g, 13 mmol) and sodium carbonate (1.94 g, 18.3 mmol) in acetone was added benzyl bromide (1.7 mL, 14 mmol). The mixture was heated to reflux for 24 h, cooled, filtered, and the solid washed with acetone. The filtrate and acetone washings were combined and concentrated in vacuo. Recrystallization from ether/hexanes gave 1.06 g (33%) of the title product as an off-white solid. MS-FD 243 m/e (M+).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe solid washed with acetone
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-975c64ed7ad244fab979da9af431510a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313122B1

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