Iodoethane → 6-Ethoxy-2,2,3,3,4,4,5,5-octafluorohexanol

HRID 1608900Notes

Reaction equation

HRID 1608900 reaction equation
[OH-].[K+].[F:3][C:4]([F:18])([C:7]([F:17])([F:16])[C:8]([F:15])([F:14])[C:9]([F:13])([F:12])[CH2:10][OH:11])[CH2:5][OH:6].[CH2:19](I)[CH3:20]>O>[CH2:19]([O:11][CH2:10][C:9]([F:12])([F:13])[C:8]([F:15])([F:14])[C:7]([F:16])([F:17])[C:4]([F:18])([F:3])[CH2:5][OH:6])[CH3:20]

Participants

5

Conditions

Temperature
90 °C

Procedure

15.4 g potassium hydroxide was dissolved in 200 ml of deionized water, 62 g of 2,2,3,3,4,4,5,5-octafluorohexane-1,6-diol [prepared essentially as described by I.L. Knunyants, L. Chih-yan and V. V. Shokina, Advances in Chem. (Uspekhi Khimi) 32, Original 1502, Eng. Trans. 461-476 (1963); Translation RSIC-165 (Redstone Information Center)] was added, and the mixture was heated to 90° C. Over a period of one hour, 35.7 g of ethyl iodide was added with rapid stirring to the flask via an addition funnel. The reaction mixture was then heated to reflux for two hours. The reaction mixture was cooled to room temperature, and the bottom product phase (54 g crude product) was split away from the aqueous layer. The crude product was distilled at 92°-100° C. at 5.5 mm Hg (5.5 torr) to give 29.1 g of 6-ethoxy-2,2,3,3,4,4,5,5-octafluorohexanol.

Workup

  1. additionTranslation RSIC-165 (Redstone Information Center)] was added
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux for two hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customthe bottom product phase (54 g crude product) was split away from the aqueous layer
  6. distillationThe crude product was distilled at 92°-100° C. at 5.5 mm Hg (5.5 torr)

Sources & evidence

ORD record
ord-9b26fa0c5e3143128ab4b9733df0593f
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

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