Trimethylhydroquinone → HCID 19438081, compound

HRID 1464494Notes

Reaction equation

HRID 1464494 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].O[CH:13]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]>CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C1(C)C=CC=CC=1>[CH3:11][C:6]1[C:7](=[O:10])[C:8]([CH3:9])=[C:2]([CH3:1])[C:3](=[O:4])[C:5]=1[CH:13]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 12785TrimethylhydroquinoneHCID 18979260HCID 18979260, compound

Product 1

HCID 19438081HCID 19438081, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

D-Camphor-10-sulfonic acid (0.1 g) was added to a toluene solution (60 ml) of 2,3,5-trimethylhydroquinone (3.1 g, 0.02 mole) and 6-hydroxy-6-(4-methoxyphenyl)hexanoic acid (5.0 g, 0.021 mole), and the mixture was heated at 70° C. for 20 hours, with stirring. The reaction solution was evaporated under reduced pressure, and tetrahydrofuran (50 ml) was added to dissolve the residue, followed by adding furthermore a 10% aqueous solution of ferric chloride and stirring at room temperature for 10 minutes. The reaction product was extracted with ethyl acetate, and the organic layer was washed with water, dried and then concentrated under reduced pressure. The residue was chromatographed on a silica gel column, and elution was performed with isopropyl ether to give 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid (5.1 g, 76%). 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. 23 to 34 and 68 were prepared.

Workup

  1. customThe reaction solution was evaporated under reduced pressure, and tetrahydrofuran (50 ml)
  2. additionwas added
  3. dissolutionto dissolve the residue
  4. additionby adding furthermore a 10% aqueous solution of ferric chloride
  5. stirringstirring at room temperature for 10 minutes
  6. extractionThe reaction product was extracted with ethyl acetate
  7. washthe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was chromatographed on a silica gel column, and elution

Sources & evidence

ORD record
ord-cf8d3c7ab09f41d5896492bc0c35d3d2
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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