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

HRID 2188796Notes

Reaction equation

HRID 2188796 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 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(4-hydroxy-3-nitrophenyl)ethanone (50.00 g, 276 mmol), sodium iodide (20.00 g, 133.4 mmol), potassium carbonate (115.00 g, 832.00 mmol), and benzyl bromide (43.00 mL, 362.00 mmol) in acetone (120 mL) was stirred under reflux for 16 h. The solids were removed by filtration and the filtrate concentrated by rotary evaporation. After this time the resulting residue was diluted with dichloromethane and insoluble inorganics were removed by filtration. The filtrate was concentrated in vacuo and the resulting residue was dissolved in hot chloroform. Hexanes were added to form a precipitate. The solids were collected by filtration to give benzyl ether 2 as a white solid (65.60 g, 87%): 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 16 h
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate concentrated by rotary evaporation
  4. additionAfter this time the resulting residue was diluted with dichloromethane and insoluble inorganics
  5. customwere removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionthe resulting residue was dissolved in hot chloroform
  8. additionHexanes were added
  9. customto form a precipitate
  10. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-b1b1ad6820cd4f95b10aae51c7c32e5f
Source dataset
uspto-grants-2012_12
Patent number
US08324218B2

Reaction notes

Loading…