Allyl chloride → HCID 12509100, compound

HRID 435882Notes

Reaction equation

HRID 435882 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:15]([Cl:18])[CH:16]=[CH2:17]>CN(C)C=O>[ClH:18].[CH2:17]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 129132492-(1H-Imidazol-1-yl)phenol

Product 1

HCID 12509100HCID 12509100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g. of 2-(1-imidazolyl)-phenol [Khim. Geterotsikl. Soedin Akad. Nauk Latv. SSR 1966, 143; Chem. Abstr. 65 (1966) 13686] is dissolved in 20 ml. of dimethylformamide and combined with 300 mg. of a sodium hydride - oil suspension (80%). The mixture is agitated for one hour at room temperature, and then 760 mg. of allyl chloride is added thereto. After three hours of agitation at room temperature, the solution is added to 100 ml. of 1N sulfuric acid and extracted with ether. The aqueous phase is rendered alkaline with 40% sodium hydroxide solution and extracted with methylene chloride. After drying and evaporation of the solvent, the crude product is dissolved in a small amount of methanol and combined with methanolic hydrochloric acid until a weakly acidic reaction is observed. After the solvent has been evaporated under vacuum, the residue is dissolved in methylene chloride and mixed with ether until the onset of crystallization.

Workup

  1. waitAfter three hours of agitation at room temperature
  2. additionthe solution is added to 100 ml
  3. extractionof 1N sulfuric acid and extracted with ether
  4. extractionextracted with methylene chloride
  5. customAfter drying
  6. customevaporation of the solvent
  7. dissolutionthe crude product is dissolved in a small amount of methanol
  8. customcombined with methanolic hydrochloric acid until a weakly acidic reaction
  9. customAfter the solvent has been evaporated under vacuum
  10. dissolutionthe residue is dissolved in methylene chloride
  11. additionmixed with ether until the onset of crystallization

Sources & evidence

ORD record
ord-2c37f6a511be4e8caec0a15d51397672
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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