N-bromobutanimide → 3-Furancarboxylic acid, 2,5-dimethyl-, ethyl ester

HRID 2398650

Reaction equation

HRID 2398650 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:2][C:1]1[O:3][C:11]([CH3:12])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54249081Ethyl 2-acetyl-2-pentenoate

Product 1

HCID 1414573-Furancarboxylic acid, 2,5-dimethyl-, ethyl esterYield 83.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.41 g (0.02 mole) ethyl 2-acetyl-2-pentenoate and 3.57 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 2 hours. After cooling, the succinimide was removed by filtration and the solution concentrated in vacuo. Distillation gave 2.8 g (83%) of ethyl 2,5-dimethyl-3-furoate, bp 96 °-100° C. (18 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated in vacuo
  6. distillationDistillation

Sources & evidence

ORD record
ord-67c5bc136b934568b8c409c5c2df7035
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Linked notes

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