2,3-Dichloropropene → HCID 22387841, compound

HRID 1072819Notes

Reaction equation

HRID 1072819 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[C:13]([CH2:15]Cl)=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:9][O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]2[O:1][C:13]([CH3:15])=[CH:14][C:11]=2[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 7456MethylparabenHCID 11430Potassium Carbonate

Product 1

HCID 22387841HCID 22387841, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
200 °C

Procedure

Methyl 4-hydroxybenzoate (25.51 g), 2,3-dichloropropene (22.33 g) and potassium carbonate (27.65 g) were heated in 2-butanone (150 ml) at 70° C. for 20 hr. The reaction mixture was concentrated, and water was added, which was followed by extraction with toluene. The extract was washed with saturated brine and concentrated. To the concentrate (34.5 g) was added diethyl aniline (100 ml) and the mixture was stirred at 200° C. for 89 hr. After cooing, toluene and concentrated hydrochloric acid were added and the toluene layer was washed with saturated brine, and dried over sodium sulfate. After concentration, formic acid (80 ml) was added to the residue (34.5 g) and the mixture was refluxed for 25 hr. After concentration, ethyl acetate and water were added. The separated toluene layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the objective compound (3.30 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionwhich was followed by extraction with toluene
  4. washThe extract was washed with saturated brine
  5. concentrationconcentrated
  6. concentrationTo the concentrate (34.5 g)
  7. additionwas added diethyl aniline (100 ml)
  8. additiontoluene and concentrated hydrochloric acid were added
  9. washthe toluene layer was washed with saturated brine
  10. dry with materialdried over sodium sulfate
  11. concentrationAfter concentration, formic acid (80 ml)
  12. additionwas added to the residue (34.5 g)
  13. temperaturethe mixture was refluxed for 25 hr
  14. concentrationAfter concentration, ethyl acetate and water
  15. additionwere added
  16. washThe separated toluene layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  17. dry with materialdried over magnesium sulfate
  18. concentrationconcentrated
  19. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d96441eeb8324261986ddbc6de6bd033
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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