Imidazole → 1-(3,7,11-Trimethyldodeca-2,6,10-trienyl)-imidazole

HRID 893975Notes

Reaction equation

HRID 893975 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3][CH2:4]Cl.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>O1CCOCC1>[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3][CH2:4][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 40734091-Chloro-3,7,11-trimethyldodeca-2,6,10-triene

Product 1

HCID 543863621-(3,7,11-Trimethyldodeca-2,6,10-trienyl)-imidazoleYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

72.3 parts by weight of 3,7,11-trimethyldodeca-2,6,10-trienyl chloride and 40.8 parts by weight of imidazole are dissolved in 500 parts by weight of dioxane. The reaction mixture is then refluxed for 6 hours. After the mixture has cooled it is filtered and the filtrate is concentrated in vacuo. Distillation of the residue from the filtrate under an oil pump vacuum gives 72 parts by weight (88% of theory) of 1-(3,7,11-trimethyldodeca-2,6,10-trienyl)-imidazole; b.p. (0.01 mm Hg): 155° C.

Workup

  1. temperatureThe reaction mixture is then refluxed for 6 hours
  2. temperatureAfter the mixture has cooled it
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. distillationDistillation of the residue from the filtrate under an oil pump vacuum

Sources & evidence

ORD record
ord-7b0cebd9e07e4f34b10aebd7b0cd86f7
Source dataset
uspto-grants-1981_08
Patent number
US04282238

Reaction notes

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