Imidazole → 4-Phenylcyclohexylmethyl iodide

HRID 2269348

Reaction equation

HRID 2269348 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39]O)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CCCCC>[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39][I:25])[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 3100608(4-Phenylcyclohexyl)methanol

Product 1

HCID 183339764-Phenylcyclohexylmethyl iodideYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

Imidazole (4.4 g, 0.065 mol) is added in one portion to a solution of triphenylphosphine (17.0 g, 0.065 mol) in dichloromethane (300 mL) at 25° C. After all of the solids dissolved, iodine (16.5 g, 0.065 mol) is added in four portions. The mixture is stirred for 10 min. then a solution of 4-phenylcyclohexylmethanol (10.5 g, 0.055 mol) is added dropwise and the mixture is stirred at 25° C. for 18 h. The reaction mixture is poured into pentane and the resulting solids filtered. The filtrate is concentrated in vacuo and the residue is dissolved in dichloromethane. This solution is poured into hexanes, the solids were filtered, and the filtrate is concentrated in vacuo. The residue is passed through a pad of silica gel using hexanes as eluent to afford 14.6 g (89%) of 4-phenylcyclohexylmethyl iodide as an oil.

Workup

  1. dissolutionAfter all of the solids dissolved
  2. stirringthe mixture is stirred at 25° C. for 18 h
  3. filtrationthe resulting solids filtered
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue is dissolved in dichloromethane
  6. additionThis solution is poured into hexanes
  7. filtrationthe solids were filtered
  8. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-41eb19a3db80431290c4337f10d21054
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Linked notes

Loading…