Imidazole → 4'-(2-Iodoethyl)octanophenone

HRID 1595064Notes

Reaction equation

HRID 1595064 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:43]I>C(OCC)(=O)C>[I:43][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 222186582-(4-Octanoylphenyl)ethanol

Product 1

HCID 111320764'-(2-Iodoethyl)octanophenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4′-(2-Hydroxy ethyl)octanophenone prepared in the step B (137 g), imidazole (53 g) and triphenyl phosphine (174 g) were dissolved in ethyl acetate (550 ml) to obtain a solution. Iodine (197 g) was added to the solution with cooling, and the solution was stirred at room temperature for 1 hour. Then the reaction solution was diluted with ethyl acetate, the solution was washed with saturated sodium sulfite solution, and saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated. The concentrated residue was extracted with hexane-ethyl acetate (20:1), and extracted solution was passed through a silica gel layer. The filtrate was concentrated to obtain 4′-(2-iodoethyl)octanophenone (175 g) in the form of white crystal.

Workup

  1. customto obtain a solution
  2. temperaturewith cooling
  3. washthe solution was washed with saturated sodium sulfite solution, and saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. extractionThe concentrated residue was extracted with hexane-ethyl acetate (20:1)
  7. extractionextracted solution
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1622a9f3ea85466eaa68caa42935a2ef
Source dataset
uspto-grants-2001_09
Patent number
US06284915B1

Reaction notes

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