Sodium Iodide → HCID 86661268, compound

HRID 514287Notes

Reaction equation

HRID 514287 reaction equation
[I-:1].[Na+].[C:3]([O:24][CH2:25]Cl)(=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(#N)C.[Al]>[C:3]([O:24][CH2:25][I:1])(=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 86661269HCID 86661269, compound

Product 1

HCID 86661268HCID 86661268, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 5359268AluminumSolvent

Conditions

Temperature
25 °C

Procedure

Sodium iodide (8.31 g, 0.0555 mol) was added to a solution of chloromethyl arachidate (6.7 g, 0.0185 mol) in acetonitrile (67 ml) at 25° C. The flask was covered in aluminum foil to protect from light and stirred at 25° C. for 16 hours. The reaction mixture was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with aqueous saturated NaHCO3, aqueous sodium sulfite (10% solution), and brine, then dried with sodium sulphate and concentrated in vacuo to provide the desired product (5.9 g, 71% yield) as a white solid which was not purified any further.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic extracts were washed with aqueous saturated NaHCO3, aqueous sodium sulfite (10% solution), and brine
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c30d826164b1416dbd1eda107ed18a60
Source dataset
uspto-grants-2015_08
Patent number
US09107911B2

Reaction notes

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