Potassium Carbonate → HCID 20207215, compound

HRID 364780Notes

Reaction equation

HRID 364780 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]([N:21]([CH2:26][CH3:27])[C:22](=[O:25])[CH2:23]Cl)[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)CC>[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:25])[N:21]([CH2:26][CH3:27])[CH2:19][CH3:20])([OH:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 20239879HCID 20239879, compound

Product 1

HCID 20207215HCID 20207215, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

5.3 g. of 1-(3-chlorophenyl)-1-(2-hydroxyphenyl)-propan-1-ol and 3.3 g. of monochloroacetic acid diethyl amide are dissolved in 36 ml. of n-propanol, and the reaction mixture is boiled for 4 hours, with stirring in the presence of 3 g. of anhydrous potassium carbonate. After cooling the solvent is distilled off under reduced pressure. To the residue water is added and it is extracted with ether. The ethereal solution is washed with water, a 5% aqueous sodium hydroxide solution and again with water until neutral. After drying over anhydrous magnesium sulfate, the solvent is distilled off in vacuo. The residue is crystallized from a mixture of n-hexane and ethyl acetate to yield 5.8 g. of the named compound, melting at 93°-94° C.

Workup

  1. temperatureAfter cooling the solvent
  2. distillationis distilled off under reduced pressure
  3. additionTo the residue water is added
  4. extractionit is extracted with ether
  5. washThe ethereal solution is washed with water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off in vacuo
  8. customThe residue is crystallized from a mixture of n-hexane and ethyl acetate
  9. customto yield 5.8 g

Sources & evidence

ORD record
ord-6e1b8eb739724e08a87860f3e357817e
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

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