2,5-Hexanedione → HCID 23000957, compound

HRID 397735Notes

Reaction equation

HRID 397735 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[CH2:6]([CH2:10][C:11](=O)[CH3:12])[C:7]([CH3:9])=O.C([O-])(=O)C.[K+]>C(O)(=O)C.O>[Br:2][CH2:3][CH2:4][N:5]1[C:11]([CH3:12])=[CH:10][CH:6]=[C:7]1[CH3:9]

Participants

6

Reactant 3

HCID 80352,5-HexanedioneHCID 517044Potassium AcetateHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 23000957HCID 23000957, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromoethylamine hydrobromide (20.5 g, 0.1 mol) and acetonylacetone (12.5 ml, 0.1 mol) in acetic acid (10 ml) was added potassium acetate (10 g, 0.1 mol), and the mixture was stirred for 1 h at 20° C. and for 2 h at 80° C. The reaction mixture was diluted with water (150 ml) and extracted with diethyl ether (150 ml). The extract was washed with brine and concentrated in vacuo to afford an oily residue. The residue was distilled at 60-64° C./0.5 mm of mercury to afford the title compound as a colourless oil (9.45 g, 47%).

Workup

  1. extractionextracted with diethyl ether (150 ml)
  2. washThe extract was washed with brine
  3. concentrationconcentrated in vacuo
  4. customto afford an oily residue
  5. distillationThe residue was distilled at 60-64° C./0.5 mm of mercury

Sources & evidence

ORD record
ord-f77421a40eff4e8187a82d6aa5ef8260
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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