Trimethylhydroquinone → HCID 15616467, compound

HRID 1646801Notes

Reaction equation

HRID 1646801 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[C:5]([CH3:11])[C:3]=1[OH:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:15][CH:14]=1>B(F)(F)F.CCOCC.C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:8]2[C:7](=[O:9])[C:6]([CH3:10])=[C:5]([CH3:11])[C:3](=[O:4])[C:2]=2[CH3:1])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 12785TrimethylhydroquinoneHCID 19088083HCID 19088083, compound

Product 1

HCID 15616467HCID 15616467, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Toluene (15 ml) was added to 0.76 g (5.0 mmole) of 2,5,6-trimethylhydroquinone and 1.28 g (5.0 mmole) of 7-(4-chlorophenyl)-7-hydroxyheptanoic acid, and the mixture was warmed at 60° C. and stirred. 0.19 ml (5.0×0.3 mmole) of boron trifluoride ethyl etherate was added to the mixture, followed by stirring at 60° C. for 15 hours. After the conclusion of the reaction, a large amount of the toluene was distilled off, and the residue was dissolved in tetrahydrofuran (20 ml). An aqueous solution (10 ml) of ferric chloride (2.7 g, 10.0 mmole 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 extract the reaction product. The organic layer was separated out, washed with aqueous sodium chloride solution and dried (magnesium sulfate). The ethyl acetate solution was chromatographed on a short silica gel (10 g) column, and elution was performed with ethyl acetate. The fractions containing the object compound were collected and concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate/isopropyl ether to give 1.52 g (78%) of 7-(4-chlorophenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)heptanoic acid.

Workup

  1. stirringby stirring at 60° C. for 15 hours
  2. customAfter the conclusion of the reaction
  3. distillationa large amount of the toluene was distilled off
  4. dissolutionthe residue was dissolved in tetrahydrofuran (20 ml)
  5. additionAn aqueous solution (10 ml) of ferric chloride (2.7 g, 10.0 mmole was added to the solution
  6. stirringby stirring at room temperature for 20 minutes
  7. distillationThe tetrahydrofuran was distilled off
  8. additionethyl acetate was added to the residue
  9. extractionto extract the reaction product
  10. customThe organic layer was separated out
  11. washwashed with aqueous sodium chloride solution
  12. dry with materialdried (magnesium sulfate)
  13. customThe ethyl acetate solution was chromatographed on a short silica gel (10 g) column, and elution
  14. additionThe fractions containing the object compound
  15. customwere collected
  16. concentrationconcentrated under reduced pressure
  17. customthe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-cf1d180d6838439a88d4a16fca027f0a
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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