Lithium Chloride → HCID 23001924, compound

HRID 398095Notes

Reaction equation

HRID 398095 reaction equation
[C:1]([CH2:14][C:15]([CH2:18][C:19](I)([F:21])[F:20])([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[Cl-].[Li+]>CN(C)C=O>[F:20][C:19]([F:21])=[CH:18][C:15]([F:16])([F:17])[CH2:14][C:1]([F:2])([F:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[C:10]([F:13])([F:12])[F:11]

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 230019271,1,1,2,2,3,3,4,4,6,6,8,8-Tridecafluoro-8-iodooctane

Product 1

HCID 23001924HCID 23001924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A round-bottomed flask was charged with a mixture of C4F9—CH2CF2—CH2CF2—I (180 g, 0.38 mol) and lithium chloride (23.9 g, 0.56 mol) in anhydrous N,N-dimethylformamide (DMF, 160 ml) solvent. The mixture flask was vigorously stirred throughout the reaction. A vacuum was applied (220-240 mm Hg) and the mixture was slowly heated up to 140° C. over the course of 1-2 hrs. A volatile component was distilled off during this heating period. It was collected in a cold trap. Redistillation afforded the desired 1,1,3,3,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octene [C4F9—CH2CF2—CH═CF2] product as a clear colorless liquid having a boiling point 80-82° C. at 230 mm Hg. The yield was 86 grams (65.4%).

Workup

  1. distillationA volatile component was distilled off during this heating period
  2. customIt was collected in a cold trap
  3. distillationRedistillation

Sources & evidence

ORD record
ord-101e7ebdee6c4c0e8d34233a7e2829dd
Source dataset
uspto-grants-2003_08
Patent number
US06610790B2

Reaction notes

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