Sulfuric Acid → HCID 20504188, compound

HRID 1702136Notes

Reaction equation

HRID 1702136 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:18])[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11].S(=O)(=O)(O)O.[OH-:24].[Na+].[C:26]1([CH3:32])C=CC=CC=1>C(Cl)Cl.C(O)CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:10]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[O:24][CH2:26][CH2:32][O:11]1)[CH3:18]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 140744312-(2,4-Dichlorophenyl)-1-(3-pyridyl)-1-propanone

Product 1

HCID 20504188HCID 20504188, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2 g of 2-(2,4-dichlorophenyl)-1-(3-pyridyl)-1-propanone are dissolved in 80 ml of toluene. After the addition of 1.05 g of concentrated sulfuric acid and 1.02 g of ethylene glycol, the mixture is heated at reflux. The water which is formed in the course of the reaction is separated using a water separator. After a reaction period of 4, 7 and 12 hours, an additional 1.5 g of ethylene glycol are added each time. After 15 hours, the mixture is cooled, the toluene phase is discarded, the lower viscous phase is diluted with 50 ml of methylene chloride and subsequently poured into 37.5 ml of 1N sodium hydroxide. Then it is back-extracted with methylene chloride and the organic phase is washed and dried over anhydrous sodium sulfate. After removal of the solvent, 3-[2-(2,4-dichloro-α-methyl-benzyl)-1,3-dioxolan-2-yl]pyridine is obtained as a brownish, highly viscous oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. customis separated
  4. customAfter a reaction period of 4, 7 and 12 hours
  5. temperaturethe mixture is cooled
  6. extractionThen it is back-extracted with methylene chloride
  7. washthe organic phase is washed
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter removal of the solvent

Sources & evidence

ORD record
ord-6b50a3965b1e4817b197368d8ede24f6
Source dataset
uspto-grants-1983_04
Patent number
US04380544

Reaction notes

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