Potassium Carbonate → alpha-Ethyl-alpha-(4-chlorophenyl)-4-[3-(di-n-propylamino)-propoxy]-benzylalcohol

HRID 236568Notes

Reaction equation

HRID 236568 reaction equation
[CH2:1]([C:3]([OH:18])([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25]([N:28]([CH2:32][CH2:33][CH2:34]Cl)[CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:1]([C:3]([OH:18])([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:27][CH2:26][CH2:25][N:28]([CH2:32][CH2:33][CH3:34])[CH2:29][CH2:30][CH3:31])=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12333917Dipropylaminopropyl chlorideHCID 14727318alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

Product 1

HCID 20216260alpha-Ethyl-alpha-(4-chlorophenyl)-4-[3-(di-n-propylamino)-propoxy]-benzylalcohol

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

13.1 g. of α-ethyl-α-(4-chlorophenyl)-4-hydroxy-benzylalcohol, 14 g. of anhydrous potassium carbonate, 9.8 g. of dipropylaminopropyl chloride and 0.85 g. of tetrabutyl ammonium hydrogensulfate in 135 ml. of ethyl acetate are slightly boiled for 20 hours, under stirring. After cooling the mixture, the solvent is evaporated in vacuo. To the residue water and benzene are added. The phases are separated, the benzene solution is washed with water, dried over anhydrous potassium carbonate, filtered and evaporated. The residue is purified by vacuum fractionation. 13.8 g. of the desired end product are obtained, boiling at 198° to 200° C./1.33 Pa.

Workup

  1. temperatureAfter cooling the mixture
  2. customthe solvent is evaporated in vacuo
  3. additionTo the residue water and benzene are added
  4. customThe phases are separated
  5. washthe benzene solution is washed with water
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by vacuum fractionation
  10. customof the desired end product are obtained

Sources & evidence

ORD record
ord-207e32b5a3714d40af02fe0ad4959c98
Source dataset
uspto-grants-1987_02
Patent number
US04645779

Reaction notes

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