Benzene → Oct-2-enal

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

Reactant 2

HCID 241Benzene

HCID 8024Vinyl ether

Product 1

HCID 16900Oct-2-enal

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

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

Sources & evidence

ORD record: ord-02021c1d77f449a1a06a2dba21ca8c66
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04045475

Reaction notes

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