Imidazole → 9-(Iodomethyl)nonadecane

HRID 1261555Notes

Reaction equation

HRID 1261555 reaction equation
[I:1]I.[CH2:3]([CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12]O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[I:1][CH2:12][CH:11]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 214142-OctyldodecanolHCID 24437Sodium Sulfite

Product 1

HCID 866914509-(Iodomethyl)nonadecaneYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (12.25 g, 48.3 mmol) was added to a solution of 2-octyl-1-dodecanol (12.42 g, 41.6 mmol), triphenylphosphine (13.17 g, 50.2 mmol), and imidazole (3.42 g, 50.2 mmol) in 80 mL dichloromethane at 0° C. After stirring for 30 min, the reaction mixture was allowed to warm to room temperature over 4 h before 12 mL of saturated Na2SO3 (aq) was added. The organics were concentrated by evaporation and the mixture taken up in 500 mL pentane, washed three times with 200 mL water, and once with 150 mL brine. The mixture was then passed through a 3 cm silica gel plug, and dried over Na2SO4. The organics were concentrated by evaporation to give a colorless oil (15.78 g, yield 92.9%).

Workup

  1. additionwas added
  2. concentrationThe organics were concentrated by evaporation
  3. washwashed three times with 200 mL water
  4. dry with materialdried over Na2SO4
  5. concentrationThe organics were concentrated by evaporation

Sources & evidence

ORD record
ord-fd77223c9fbe4eb6bbd3132c2c713f51
Source dataset
uspto-grants-2013_06
Patent number
US08470961B2

Reaction notes

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