Benzene → 4-Cyclobutyl-3-buten-2-one

HRID 615457Notes

Reaction equation

HRID 615457 reaction equation
[CH:1]1([C:5](Cl)=O)[CH2:4][CH2:3][CH2:2]1.C1(P(=[CH:27][C:28](=[O:30])[CH3:29])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>O1CCCC1.[Pd]>[CH:1]1([CH:5]=[CH:27][C:28](=[O:30])[CH3:29])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 241BenzeneHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 566220724-Cyclobutyl-3-buten-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10 parts of cyclobutylcarboxylic acid chloride in tetrahydrofuran is hydrogenated over 10% palladium on carbon catalyst, to provide cyclobutylcarboxaldehyde. 25 parts of triphenylphosphoranylidene-2-propanone and 6.3 parts of the cyclobutylcarboxaldehyde in 60 parts by volume of benzene under nitrogen are refluxed for 8 hours. The solvent is removed by evaporation under reduced pressure to provide 4-cyclobutyl-3-buten-2-one.

Workup

  1. customto provide cyclobutylcarboxaldehyde
  2. customThe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7418a28804a240dfad2184794433063d
Source dataset
uspto-grants-1985_02
Patent number
US04499296

Reaction notes

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