Imidazole → 3,7,11-Trimethyl-1-dodecyl iodide

HRID 1819549Notes

Reaction equation

HRID 1819549 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15]O)[CH3:13])[CH3:8])[CH3:3].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:41]I>C1(C)C=CC=CC=1.CCCCCC>[CH3:13][CH:12]([CH2:11][CH2:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:14][CH2:15][I:41]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 1388243,7,11-Trimethyl-1-dodecanol

Product 1

HCID 578873113,7,11-Trimethyl-1-dodecyl iodideYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a stirring solution of 44 (1.5 g, 6.6 mmol), imidazole (1.13 g, 16.6 mmol, 2.5 equ) and triphenylphosphine (4.40 g, 16.8 mmol, 2.5 equ) in toluene (250 ml) under nitrogen was added iodine (3.26 g, 12.8 mmol, 1.9 equ). The reaction mixture was stirred for one hour then filtered. The filtrate was washed with 8% sodium thiosulphate solution (250 ml) and brine (100 ml) then dried (Na2SO4) and concentrated in vacuo to give a white solid. This solid was taken up in hexane, cooled and filtered. The filtrate was then concentrated in vacuo to give 46 (1.1 g, 61%) as a colourless oil.

Workup

  1. filtrationthen filtered
  2. washThe filtrate was washed with 8% sodium thiosulphate solution (250 ml) and brine (100 ml)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a white solid
  6. temperaturecooled
  7. filtrationfiltered
  8. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-fc4cd3b027a04ea39799505ca8f5eb8d
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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