N-bromobutanimide → HCID 21433410, compound

HRID 2398658Notes

Reaction equation

HRID 2398658 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:12]([C:11]1[O:3][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2765162-Decenoic acid, 2-acetyl-, ethyl ester

Product 1

HCID 21433410HCID 21433410, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4.80 g (0.02 mole) ethyl 2-acetyl-2-decenoate and 3.56 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 12 hours. After cooling, the succinimide was removed by filtration and the solution concentrated by rotary evaporation. Distillation of the crude product gave 4.20 g (88%) of ethyl 5-hexyl-2-methyl-3-furoate, bp 107°-109° C. (0.4 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated by rotary evaporation
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-06460bb17f784183b5bd5beb99812f08
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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