N-bromobutanimide → HCID 12452844, compound

HRID 2398660Notes

Reaction equation

HRID 2398660 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[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][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53678912HCID 53678912, compound

Product 1

HCID 12452844HCID 12452844, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2.64 g (8.15 mmole) ethyl 2-acetyl-2-hexadecenoate and 1.45 g (8.15 mmole) N-bromosuccinimide in 25 ml of carbon tetrachloride was heated at reflux for 12 hours. After cooling, the succinimide was removed by filtration and the solution concentrated in vacuo. Distillation of the crude product gave 1.65 g (63%) of ethyl 5-dodecyl-2-methyl-3-furoate, bp 160°-163° 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 in vacuo
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-27403d0513cf401a84db85a6eff3e31a
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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