Potassium Iodide → 1-(2-Hydroxy-4-((4-methoxyphenyl)methoxy)phenyl)ethanone

HRID 14481

Reaction equation

HRID 14481 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 69902',4'-DihydroxyacetophenoneHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 113232321-(2-Hydroxy-4-((4-methoxyphenyl)methoxy)phenyl)ethanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2′,4′-Dihydroxyacetophenone (11.71 g, 0.077 mol), 4-methoxybenzyl chloride (10.44 ml, 0.077 mol), anhydrous potassium carbonate (11.75 g, 0.085 mol) and potassium iodide (12.78 g, 0.077 mol) are heated together in refluxing dry acetone (80 ml) for 4 hours. The mixture is then cooled to room temperature, poured into water (250 ml) and extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts are combined, washed with saturated brine (100 ml), dried (MgSO4), filtered and concentrated, until crystallization commences. After standing at 4° C. for 16 h, the crystals are recovered by filtration, washed with cold ethyl acetate and then with n-hexane and dried.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washwashed with saturated brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated, until crystallization commences
  6. filtrationthe crystals are recovered by filtration
  7. washwashed with cold ethyl acetate
  8. dry with materialwith n-hexane and dried

Sources & evidence

ORD record
ord-7b4b11184e3f449b88142c800caa6db1
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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