Toluene → HCID 15229489, compound

HRID 1646786Notes

Reaction equation

HRID 1646786 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[C:15]([CH3:16])=[C:14]([OH:17])[C:13]([CH3:18])=[CH:12][C:10]=1[OH:11].C(O[CH:23]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=O)C>CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C(O)C>[CH3:18][C:13]1[C:14](=[O:17])[C:15]([CH3:16])=[C:9]([CH3:8])[C:10](=[O:11])[C:12]=1[CH:23]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

6

Reactant 3

HCID 1140TolueneHCID 12785TrimethylhydroquinoneHCID 15229488HCID 15229488, compound

Product 1

HCID 15229489HCID 15229489, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

D-Camphor-10-sulfonic acid (0.1 g) was added to a toluene solution (50 ml) of 2,3,5-trimethylhydroquinone (3.1 g, 0.02 mole) and ethyl 6-acetoxy-6-(2-thienyl)hexanoate (5.6 g, 0.02 mole), and the mixture was heated at 60° C. for 6.5 hours, with stirring. After cooling, ethanol (100 ml) and a 10% aqueous solution (20 ml) of ferric chloride were added to the reaction solution, followed by stirring for 10 minutes. The reaction product was extracted with isopropyl ether, and the organic layer was washed with water, dried (over magnesium sulfate) and concentrated under reduced pressure. The residue was chromatographed on a silica gel column, and elution was performed with isopropyl etherhexane (1:1) to give ethyl 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-(2-thienyl)hexanoate (5.6 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. 2 to 8 were prepared.

Workup

  1. temperatureAfter cooling
  2. stirringby stirring for 10 minutes
  3. extractionThe reaction product was extracted with isopropyl ether
  4. washthe organic layer was washed with water
  5. dry with materialdried (over magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column, and elution

Sources & evidence

ORD record
ord-ce2650c53a06450c9afa513409879ae9
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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