Boron trifluoride etherate → HCID 15229494, compound

HRID 1646787Notes

Reaction equation

HRID 1646787 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1[OH:4].C(O[CH:16]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=O)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[C:26]1([CH:16]([C:5]2[C:3](=[O:4])[C:2]([CH3:1])=[C:8]([CH3:9])[C:7](=[O:10])[C:6]=2[CH3:11])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12785TrimethylhydroquinoneHCID 15229503HCID 15229503, compound

Product 1

HCID 15229494HCID 15229494, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3,5-Trimethylhydroquinone (3.1 g, 0.02 mole) and 8-acetoxy-8-phenyloctanoic acid (6.0 g, 0.021 mole) were added to toluene (80 ml), and boron trifluoride ethyl etherate (0.3 ml) was added dropwise to the mixture at room temperature, with stirring. The reaction solution was stirred at room temperature for 4 days, and then the solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (50 ml), and a 10% aqueous solution of ferric chloride was added to the solution to conduct oxidation to the quinone derivative. The reaction product was extracted twice with ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. The resulting crude product was chromatographed on a silica gel column, followed by elution with isopropyl ether, and the quinone derivative was recrystallized from isopropyl ether to give 8-phenyl-8-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)octanoic acid (5.8 g, 78%). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound Nos. 10 to 19, 50 and 51 were prepared.

Workup

  1. additionwas added dropwise to the mixture at room temperature
  2. stirringThe reaction solution was stirred at room temperature for 4 days
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  5. additiona 10% aqueous solution of ferric chloride was added to the solution
  6. extractionThe reaction product was extracted twice with ethyl acetate
  7. washthe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting crude product was chromatographed on a silica gel column
  11. washfollowed by elution with isopropyl ether
  12. customthe quinone derivative was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-68409ed9b5e4498492da16a48266bf98
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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