Ethylene Glycol → HCID 56639316, compound

HRID 255843Notes

Reaction equation

HRID 255843 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][C:19]([OH:30])([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C:20](=O)[CH2:21][CH3:22].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]1[O:4][C:21]([CH2:20][C:19]([OH:30])([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[Cl:10])([CH3:22])[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 20164655HCID 20164655, compound

Product 1

HCID 56639316HCID 56639316, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

27 ml of ethylene glycol and 0.8 ml of concentrated sulphuric acid are added to a solution of 5 g of 5-(2,4-dichlorophenyl)-4-hydroxy-4-(3-pyridyl)-3-pentanone (see Example 1, 3rd end product) in 90 ml of toluene and the reaction mixture is heated at reflux temperature for 24 hours on a water separator. After cooling to room temperature the mixture is neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, the solvent is removed by evaporation under reduced pressure and the residue is recrystallized from methylene chloride/n-hexane. In this manner there are obtained 5.3 g of 5-(2,4-dichlorophenyl)-4-hydroxy-4-(3-pyridyl)-2-pentanone ethylene ketal as colorless crystals, m.p. 136°-137° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. customthe solvent is removed by evaporation under reduced pressure
  5. customthe residue is recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-ac6a6ea55c054ce1a080e381118ba407
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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