Iodine → Heptadecane

HRID 979411

Reaction equation

HRID 979411 reaction equation
ON1C=CC=CC1=S.C(Cl)(Cl)=O.[C:13](O)(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]C.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.II.[F-].[K+]>C1C=CC=CC=1.ClC(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

11

Reactant 7

HCID 807IodineHCID 1570PyrithioneHCID 5281Stearic AcidHCID 5948TributylstannaneHCID 6371PhosgeneHCID 6547AzobisisobutyronitrileHCID 522689Potassium Fluoride

Product 1

HCID 12398HeptadecaneYield 70%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent4×HCID 1049PyridineSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

140 mg (1.1 mmol) of N-hydroxypyridine-2-thione in 5 ml of benzene are added dropwise at room temperature under an atmosphere of nitrogen to a solution of 120 mg (1.2 mmol) of phosgene in 5 ml of benzene, and this leads to the instantaneous precipitation of a white solid. 286 mg (1 mmol) of stearic acid and 0.5 ml of pyridine are added in 5 ml of benzene, and the reaction medium is taken to reflux for 4 hours. 3 mmol of tri-n-butylstannane in 5 ml of benzene with 10 mg of AIBN are added to the reaction medium during 10 minutes and refluxing is maintained for 2 and half hours. The reaction is carried out in the presence of tetrachloromethane, iodine and potassium fluoride, as indicated earlier. By filtration on silica (100% pentane), 168 mg of n-heptadecane are obtained. Yield 70%.

Workup

  1. customthis leads to the instantaneous precipitation of a white solid
  2. temperatureto reflux for 4 hours
  3. temperaturerefluxing
  4. temperatureis maintained for 2 and half hours
  5. filtrationBy filtration on silica (100% pentane), 168 mg of n-heptadecane
  6. customare obtained

Sources & evidence

ORD record
ord-a3a33492abd14ad6a02d0bae943facff
Source dataset
uspto-grants-1987_05
Patent number
US04668356

Linked notes

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