Toluene → HCID 86745472, compound

HRID 1586720Notes

Reaction equation

HRID 1586720 reaction equation
[CH3:1][CH2:2][C:3](=[O:14])[CH:4]=[CH:5][C:6](=[O:13])[CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH3:12].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[K+]>O1CCCC1>[CH3:1][CH2:2][CH:3]([OH:14])[CH:4]=[CH:5][CH:6]([OH:13])[CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 86745473HCID 86745473, compound

Product 1

HCID 86745472HCID 86745472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tricyclo[6.2.2.0]dodeca-4,9-diene-3,6-dione (2.55 g) was combined with toluene (500 ml) and 1M diisobutylaluminum hydride in tetrahydrofuran (30 ml) and the mixture was stirred at room temperature for 3 hours. The solution was cooled in an ice bath and 30% potassium hydroxide solution was added. The resulting mixture was stirred for 30 minutes and the layers separated. The aqueous layer was extracted with ether (2×100 ml) and the combined organic layers were concentrated on a rotary evaporator. The residue was recrystallized from hexane/ethyl acetate to provide the product as a white solid.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringThe resulting mixture was stirred for 30 minutes
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with ether (2×100 ml)
  5. concentrationthe combined organic layers were concentrated on a rotary evaporator
  6. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-456e5eb3331d49e2bba48c1c5bc69f93
Source dataset
uspto-grants-1993_06
Patent number
US05215992

Reaction notes

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