Water → HCID 20026685, compound

HRID 1723064Notes

Reaction equation

HRID 1723064 reaction equation
ClC1C=C(Cl)C=CC=1C[C:5]1[C:10]([C:11]([C:13]2[C:14]([CH2:19][C:20]3C=C[C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=NC=CC=2)=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1.[C:33]1([CH3:43])C=CC(S(O)(=O)=O)=C[CH:34]=1.[OH2:44].[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:26][C:23]1[CH:22]=[C:21]([Cl:27])[CH:20]=[CH:19][C:14]=1[CH2:13][C:11]1([C:10]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[O:12][CH:33]([CH3:43])[CH2:34][O:44]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 54292506HCID 54292506, compound

Product 1

HCID 20026685HCID 20026685, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

13.3 g of 2,4-dichlorobenzyl-3-pyridyl ketone, 7.6 g of propanediol-1,2 and 13.0 g of p-toluenesulfonic acid are boiled in 150 ml of xylene for 32 h in a water separator. After cooling to RT, the reaction mixture is poured into 600 ml of 2N sodium hydroxide solution, and extracted 3 times with 200 ml of ether each time. The combined organic phases are washed with 250 ml of water, dried over sodium sulfate and filtered. The solvent is evaporated off and the oily crude product is purified by column chromatography (eluant: ether). The compound is obtained as clear colourless oil; nD22.5 :1.5676.

Workup

  1. extractionextracted 3 times with 200 ml of ether each time
  2. washThe combined organic phases are washed with 250 ml of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent is evaporated off
  6. customthe oily crude product is purified by column chromatography (eluant: ether)
  7. customThe compound is obtained as clear colourless oil

Sources & evidence

ORD record
ord-7d4beeed5ad34b98971ca4dfa0ad0e67
Source dataset
uspto-grants-1989_08
Patent number
US04859687

Reaction notes

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