Chlorine → 1-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-one

HRID 2164939Notes

Reaction equation

HRID 2164939 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[Cl:15]Cl>C(Cl)(Cl)Cl>[Cl:15][C:5]1[C:6]([OH:11])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]([OH:1])=[C:3]([C:12](=[O:14])[CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 133891721-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5.0 g (0.026 mol) of 1-(2,4-dihydroxy-3-propylphenyl)ethanone in 125 ml of chloroform was added 32.3 ml of (0.030 mol) 0.94M chlorine in chloroform dropwise at 25°. The mixture was stirred at 25° for 2.5 hours. The solvent was removed in vacuo and the residue was extracted with hot hexane. The hexane extract was boiled down to 100 ml and allowed to crystallize. Filtration gave 3.0 g, melting point 96°. (51% yield) of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with hot hexane
  3. extractionThe hexane extract
  4. customto crystallize
  5. filtrationFiltration
  6. customgave 3.0 g, melting point 96°

Sources & evidence

ORD record
ord-5438da4e9d554873aa15eea64d3849a9
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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