N-bromobutanimide → 3-Acetyl-2,5-dimethylfuran

HRID 2398666Notes

Reaction equation

HRID 2398666 reaction equation
[C:1]([C:4](=[CH:8][CH2:9][CH3:10])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:2][C:1]([C:4]1[CH:8]=[C:9]([CH3:10])[O:7][C:5]=1[CH3:6])=[O:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12410986HCID 12410986, compound

Product 1

HCID 615273-Acetyl-2,5-dimethylfuranYield 66%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2.80 g (0.02 mole) 3-acetyl-3-hexen-2-one and 3.56 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 24 hours. After cooling, the succinimide was removed by filtration and the solution concentrated. Distillation of the crude product gave 1.81 g (66%) of 2,5-dimethyl-3-furyl methyl ketone, bp 84°-87° C (17 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-0ff33eeab8b64a40835f69888b6a5d87
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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