Iodoethane → HCID 20082754, compound

HRID 1608895Notes

Reaction equation

HRID 1608895 reaction equation
[OH-].[K+].[F:3][C:4]([F:15])([C:7]([F:14])([F:13])[C:8]([F:12])([F:11])[CH2:9][OH:10])[CH2:5][OH:6].[CH2:16](I)[CH3:17]>O>[F:3][C:4]([F:15])([C:7]([F:13])([F:14])[C:8]([F:12])([F:11])[CH2:9][O:10][CH2:16][CH3:17])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 67831Hexafluoroamylene glycol

Product 1

HCID 20082754HCID 20082754, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

30.8 g potassium hydroxide was dissolved in 400 ml of water, 100 g (0.4715 moles) of 2,2,3,3,4,4-hexafluoropentane-1,5-diol (prepared essentially as described supra) was added, and the resulting mixture was heated to 90° C. Over a period of one hour, 74.9 g (0.480 moles) of ethyl iodide was added to the flask via an addition funnel with rapid stirring. The reaction flask was then heated to reflux for two hours. The reaction mixture was cooled to room temperature, and the bottom product phase (87.1 g) was split away from the aqueous layer. The crude product was distilled at 6.0 mm Hg (6.0 torr) to give 58.8 g of 2,2,3,3,4,4-hexafluoro-5-ethoxypentanol distilling at 85°-91° C. (conversion=68%; yield based on converted material=76%).

Workup

  1. additionwas added
  2. temperatureThe reaction flask was then heated
  3. temperatureto reflux for two hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customthe bottom product phase (87.1 g) was split away from the aqueous layer
  6. distillationThe crude product was distilled at 6.0 mm Hg (6.0 torr)

Sources & evidence

ORD record
ord-02e2745b787e445b8922f33b10980290
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

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