Benzene → HCID 12877518, compound

HRID 1758105Notes

Reaction equation

HRID 1758105 reaction equation
C1C=CC=CC=1.[OH:7][CH:8]1[CH:12]([CH2:13][CH:14]=[CH2:15])[C:11](=[O:16])[CH:10]=[CH:9]1.[Al]>CC(C)=O>[O:7]=[C:8]1[CH:12]([CH2:13][CH:14]=[CH2:15])[C:11](=[O:16])[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 5359268AluminumHCID 12877516HCID 12877516, compound

Product 1

HCID 12877518HCID 12877518, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a mixture of 150 ml of dried benzene and 100 ml of acetone, was dissolved 1.5 g of 4-hydroxy-5-allyl-2-cyclopentenone. After adding 3 g of freshly distilled aluminum isoproproxide, the mixture was heated under reflux for 12 hours. The reaction mixture was cooled to room temperature, washed twice with 30% sulfuric acid, then with water until the washings had become neutral. After drying over anhydrous sodium sulfate, the mixture was stripped of the solvent by distillation and the residue was distilled in vacuo to obtain 1.2 g (81% yield) of 4-keto-5-allyl-2-cyclopentenone boiling at 53° C./4 mmHg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. washwashed twice with 30% sulfuric acid
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe mixture was stripped of the solvent by distillation
  6. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-abdacfdea5eb47df9e7b6c58774a0532
Source dataset
uspto-grants-1983_02
Patent number
US04371711

Reaction notes

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