1,5-Dibromohexane → HCID 12385316, compound

HRID 1863123Notes

Reaction equation

HRID 1863123 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([Br:8])[CH3:7].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CC(C)=O>[Br:8][CH:6]([CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:19]

Participants

4

Reactant 2

HCID 5434851,5-DibromohexaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 12385316HCID 12385316, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1,5-dibromohexane (21.6 g, 0.09 mole) in acetone (75 ml) containing potassium phthalimide (12.3 g, 0.066 mole) was heated at reflux for 24 hr. The mixture was cooled, filtered and concentrated. The excess dibromide was recovered (6.3 g) via distillation at 1.5 mm, 130° internal temperature, and recycled. The total yield of crude product was 20.6 g (74%), mp 48°-51°. This material was used as such in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe excess dibromide was recovered (6.3 g)
  7. distillationvia distillation at 1.5 mm, 130° internal temperature

Sources & evidence

ORD record
ord-9a4eacd55a62450d9ccd2daf1fb80ce6
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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