Sodium Iodide → 1-(3-Nitro-4-phenylmethoxyphenyl)ethanone

HRID 1696822Notes

Reaction equation

HRID 1696822 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[CH2:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanoneYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(4-hydroxy-3-nitrophenyl)ethanone (5.92 g, 32.70 mmol), sodium iodide (4.90 g, 32.70 mmol), potassium carbonate (13.55 g, 98.00 mmol), and benzyl bromide (5.04 mL, 42.50 mmol) in acetone (120 mL) was stirred under reflux for 66 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were filtered off. The filtrate was concentrated in vacuo and the resulting residue was purified by flash silica gel column chromatography eluting with dichloromethane to give benzyl ether 2 as a white solid (8.24 g, 93%): 1H NMR (500 MHz, CDCl3) δ 2.60 (s, 3H), 5.32 (s, 2H), 7.18 (d, 1H), 7.41 (m, 5H), 8.12 (dd, 1H), 8.44 (d, 1H).

Workup

  1. temperatureunder reflux for 66 h
  2. customAfter removal of solvent
  3. customby rotary evaporation
  4. additionthe resulting residue was diluted with dichloromethane and insoluble inorganics
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by flash silica gel column chromatography
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-91335a284c02498992efc1d8ff0f60ce
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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