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

HRID 427608

Reaction equation

HRID 427608 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 181745022-Benzyloxy-1-methyl-4-nitro-benzeneYield 33.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-975c64ed7ad244fab979da9af431510a
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Linked notes

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