Potassium Iodide → HCID 10880888, compound

HRID 885016Notes

Reaction equation

HRID 885016 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 10880888HCID 10880888, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Bromophenol (25.00 g, 145 mmol), para-methoxybenzyl chloride (24.89 g, 159 mmol), potassium iodide (2.17 g, 14.45 mmol), and potassium carbonate (39.9 g, 289 mmol) in acetone (600 mL) was heated to reflux for 18 h. The crude reaction mixture was then cooled to room temperature and filtered through a sintered glass funnel. The filtrate was concentrated in vacuo, and the white solid was recrystallized from ethanol yielding the product as a white solid (33.44 g, 79%). 1H NMR (300 MHz, CDCl3) δ 3.80 (s, 3H), 4.95 (s, 2H), 6.85 (d, 2H), 6.92 (d, 2H), 7.32-7.40 (m, 4H).

Workup

  1. temperatureto reflux for 18 h
  2. customThe crude reaction mixture
  3. filtrationfiltered through a sintered glass funnel
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe white solid was recrystallized from ethanol yielding the product as a white solid (33.44 g, 79%)

Sources & evidence

ORD record
ord-f1fec0feae3d4ea3a506146945081d16
Source dataset
uspto-grants-2012_08
Patent number
US08242109B2

Reaction notes

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