Ethanol → HCID 14512773, compound

HRID 257247Notes

Reaction equation

HRID 257247 reaction equation
[Cl:1][C:2]([F:16])([F:15])[C:3]([Cl:14])([F:13])[C:4]([F:12])([F:11])[C:5]([F:10])([F:9])[CH2:6][CH2:7]I.C(O)C.[OH-].[K+]>O>[Cl:14][C:3]([F:13])([C:2]([Cl:1])([F:15])[F:16])[C:4]([F:11])([F:12])[C:5]([F:10])([F:9])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 18964077HCID 18964077, compound

Product 1

HCID 14512773HCID 14512773, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 1,2-dichloro-1,1,2,3,3,4,4,-heptafluoro-6-iodohexane (370.0 g) and ethanol (400 mL) was added dropwise a solution of potassium hydroxide (56.0 g), ethanol (300 mL) and water (20 mL) at 80°-90° C. over 40 minutes. After the addition was complete, the reaction mixture was refluxed for 1 hour and then poured into water. Lower layer was separated and washed with water to give desired product (233.5 g). 19F NMR: -63.9 (m, 2F), -111.9 (m, 2F), -116.2 (m, 2F), -130.5 (m, 1F); 1H NMR: 5.72 to 6.10 (m). IR: 1651 (m), 1422 (s), 1180 (s), 1055 (s), 1019 (s), 1002 (s), 980 (s).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was refluxed for 1 hour
  3. customLower layer was separated
  4. washwashed with water

Sources & evidence

ORD record
ord-51abbd3b9c1d4d3eb42c0a8e87597d6b
Source dataset
uspto-grants-1993_11
Patent number
US05260492

Reaction notes

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