Potassium Iodide → 1-(2-Methoxyphenyl)-1-[4-(3-phenylpropoxy)-phenyl]-propan-1-ol

HRID 364776Notes

Reaction equation

HRID 364776 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)([OH:12])[CH2:10][CH3:11].[C:20]1([CH2:26][CH2:27][CH2:28]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:28][CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)([OH:12])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 14727321alpha-Ethyl-alpha-(2-methoxyphenyl)-4-hydroxy-benzylalcohol

Product 1

HCID 202398721-(2-Methoxyphenyl)-1-[4-(3-phenylpropoxy)-phenyl]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.45 g. of 1-(2-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-ol, 5.5 g. of 3-phenylpropyl bromide, 6.5 g. of anhydrous potassium carbonate, 0.5 g. of potassium iodide and 65 ml. of dry acetone are slightly boiled for 15 hours, with stirring. After cooling, acetone is distilled off under reduced pressure, to the residue water is added and it is extracted with benzene. The organic phase is washed to neutral with water, a 5% aqueous sodium hydroxide solution and again water. After drying over anhydrous magnesium sulfate the solution is evaporated in vacuo. The residue is crystallized from n-hexane to yield 7.8 g. of the named compound, melting at 75°-76° C.

Workup

  1. temperatureAfter cooling
  2. distillationacetone is distilled off under reduced pressure, to the residue water
  3. additionis added
  4. extractionit is extracted with benzene
  5. washThe organic phase is washed to neutral with water
  6. dry with materialAfter drying over anhydrous magnesium sulfate the solution
  7. customis evaporated in vacuo
  8. customThe residue is crystallized from n-hexane
  9. customto yield 7.8 g

Sources & evidence

ORD record
ord-9e3d53cde45f433ba65cd38e51d2cc18
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

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