1,2-Dichloroethane → HCID 19801187, compound

HRID 1646804Notes

Reaction equation

HRID 1646804 reaction equation
ClCCCl.[CH3:5][C:6]1[C:7]([OH:15])=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:12]=1)[OH:11].[F:16][C:17]([F:35])([F:34])[C:18]1[CH:19]=[C:20]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:21]=[CH:22][CH:23]=1.B(F)(F)F.CCOCC>O>[F:16][C:17]([F:34])([F:35])[C:18]1[CH:19]=[C:20]([CH:24]([C:12]2[C:10](=[O:11])[C:9]([CH3:13])=[C:8]([CH3:14])[C:7](=[O:15])[C:6]=2[CH3:5])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8000Boron trifluoride etherateHCID 12785TrimethylhydroquinoneHCID 19088058HCID 19088058, compound

Product 1

HCID 19801187HCID 19801187, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1,2-Dichloroethane (15 ml) was added to 0.76 g (5.0 mmole) of trimethylhydroquinone and 1.45 g (5.0 mmole) of 7-(3-trifluoromethylphenyl)-7-hydroxyheptanoic acid, and the mixture was warmed to 80° C. under stirring and admixed with 0.19 ml (5.0×0.3 mmole) of boron trifluoride ethyl etherate, followed by stirring at 80° C. for 2 hours. After the reaction solution was cooled by standing at room temperature, the solvent was distilled off, and the residue was dissolved in tetrahydrofuran (15 ml). A solution of 2.7 g (10.0 mmole) of ferric chloride in water (10 ml) was added to the solution, followed by stirring at room temperature for 20 minutes. The tetrahydrofuran was distilled off, and ethyl acetate was added to the residue to carry out extraction. The organic layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated, and the residue was chromatographed on a silica gel column chromatography, followed by elution with isopropyl ether. The fractions containing the object compound were collected and concentrated under reduced pressure, and the residue was recrystallized from isopropyl ether-hexane to give 0.50 g (24%) of 7-(3-trifluoromethylphenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)heptanoic acid.

Workup

  1. stirringby stirring at 80° C. for 2 hours
  2. temperatureAfter the reaction solution was cooled
  3. customby standing at room temperature
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in tetrahydrofuran (15 ml)
  6. stirringby stirring at room temperature for 20 minutes
  7. distillationThe tetrahydrofuran was distilled off
  8. additionethyl acetate was added to the residue
  9. extractionextraction
  10. customThe organic layer was separated out
  11. washwashed with aqueous sodium chloride solution
  12. dry with materialdried (magnesium sulfate)
  13. customevaporated
  14. customthe residue was chromatographed on a silica gel column chromatography
  15. washfollowed by elution with isopropyl ether
  16. additionThe fractions containing the object compound
  17. customwere collected
  18. concentrationconcentrated under reduced pressure
  19. customthe residue was recrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-f878f23e43484f148781d3774ba6f957
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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