Benzene → 2-Octenal

HRID 442410Notes

Reaction equation

HRID 442410 reaction equation
C([O:3][CH:4]=[CH2:5])=C.[CH:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH:4](=[O:5])[CH:3]=[CH:10][CH2:11][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 241BenzeneHCID 8024Vinyl ether

Product 1

HCID 169002-Octenal

Procedure

The above vinyl ether was dissolved in benzene (100 ml.) and the solution was refluxed for 120 hours under Argon. The solvent was removed at reduced pressure to give a yellow oil (~ 1.289 g.). This was chromatographed on 25 g. of silica gel and elution with 1:9 parts by volume of ether:petroleum ether (b.p. 30°-60°) gave 792 mg. of material. This was further purified by Kugelrohr distillation at 36°/0.5 mmHg to yield 3(S),7-dimethyl-4trans)octenal as a colorless oil, [α] D25 + 30.18° (c= 3.572, CHCl3).

Workup

  1. temperaturethe solution was refluxed for 120 hours under Argon
  2. customThe solvent was removed at reduced pressure
  3. customto give a yellow oil (~ 1.289 g.)
  4. customThis was chromatographed on 25 g
  5. washof silica gel and elution with 1:9 parts by volume of ether
  6. custompetroleum ether (b.p. 30°-60°) gave 792 mg
  7. distillationThis was further purified by Kugelrohr distillation at 36°/0.5 mmHg

Sources & evidence

ORD record
ord-02021c1d77f449a1a06a2dba21ca8c66
Source dataset
uspto-grants-1977_08
Patent number
US04045475

Reaction notes

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