Hydrochloric Acid → HCID 14651334, compound

HRID 1464495Notes

Reaction equation

HRID 1464495 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:12]([CH3:13])=[C:11]([OH:14])[C:10]([CH3:15])=[CH:9][C:7]=1[OH:8].[C:16]1([CH:22]2[O:27][C:25](=[O:26])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>ClCCCl>[CH3:15][C:10]1[C:11](=[O:14])[C:12]([CH3:13])=[C:6]([CH3:5])[C:7](=[O:8])[C:9]=1[CH:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12785TrimethylhydroquinoneHCID 13884gamma-Phenyl-gamma-butyrolactoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14651334HCID 14651334, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

Aluminum chloride (1.4 g, 0.01 mole) was added to a 1,2-dichloroethane solution (20 ml) of 2,3,5-trimethylhydroquinone (1.5 g, 0.01 mole) and the mixture was heated at 80° C. A 1,2-dichloroethane solution (10 ml) of 4-phenylbutyrolactone (1.6 g, 0.01 mole) was added dropwise to the mixed solution over the 2-hours period, and the reaction was carried out under the same conditions for further 18 hours. After cooling, 2N-hydrochloric acid (40 ml) was added to the reaction solution, followed by stirring for 10 minutes, and the reaction product was extracted with isopropyl ether. The organic layer was washed with water, dried and evaporated and the residue was dissolved in tetrahydrofuran (30 ml). A 10% aqueous solution (5 ml) of ferric chloride was added to the solution, followed by stirring at room temperature for 10 minutes, and the reaction product was extracted twice with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure, and the residue was chromatographed on a silica gel column, followed by elution with isopropyl ether to give 4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-4-phenylbutyric acid (1.2 g, 38%). 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. 36 to 38 were prepared.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction product was extracted with isopropyl ether
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. dissolutionthe residue was dissolved in tetrahydrofuran (30 ml)
  7. additionA 10% aqueous solution (5 ml) of ferric chloride was added to the solution
  8. stirringby stirring at room temperature for 10 minutes
  9. extractionthe reaction product was extracted twice with ethyl acetate
  10. washThe organic layer was washed with water
  11. customdried
  12. concentrationconcentrated under reduced pressure
  13. customthe residue was chromatographed on a silica gel column
  14. washfollowed by elution with isopropyl ether

Sources & evidence

ORD record
ord-f4634a81651649b5b0667b5f3bfbda92
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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