Potassium Iodide → HCID 20207220, compound

HRID 364779Notes

Reaction equation

HRID 364779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])([OH:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])([OH:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 20239879HCID 20239879, compound

Product 1

HCID 20207220HCID 20207220, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5.3 g. of 1-(3-chlorophenyl)-1-(2-hydroxyphenyl)-propan-1-ol and 3.8 g. of monobromoacetic acid ethyl ester in 60 ml. of dry acetone is boiled in the presence of 0.8 g. of potassium iodide and 6 g. of anhydrous potassium carbonate for 5 hours, with stirring. After cooling the reaction mixture solvent is distilled off under reduced pressure, to the residue water is added and it is extracted with benzene. The benzene phase is extracted with water and a 5% aqueous sodium hydroxide solution, washed to neutral with water and dried over anhydrous magnesium sulfate. Benzene is then distilled off in vacuo and the residue is crystallized from n-hexane. 5.6 g. of the named compound are obtained, melting at 83°-84° C.

Workup

  1. temperatureAfter cooling the reaction mixture solvent
  2. distillationis distilled off under reduced pressure, to the residue water
  3. additionis added
  4. extractionit is extracted with benzene
  5. extractionThe benzene phase is extracted with water
  6. washa 5% aqueous sodium hydroxide solution, washed to neutral with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationBenzene is then distilled off in vacuo
  9. customthe residue is crystallized from n-hexane
  10. customof the named compound are obtained

Sources & evidence

ORD record
ord-bbc831cde48f40428e4bbb0d51d271dd
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

Loading…