Potassium Hydroxide → 3-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyloxymethyl)-3-methyloxetane

HRID 844478Notes

Reaction equation

HRID 844478 reaction equation
Br[CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[F:8][C:9]([F:31])([C:12]([F:30])([F:29])[C:13]([F:28])([F:27])[C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:10][OH:11].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:8][C:9]([F:31])([C:12]([F:29])([F:30])[C:13]([F:27])([F:28])[C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:10][O:11][CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 67543(Perfluoroheptyl)methanolHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

Product 1

HCID 222471223-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyloxymethyl)-3-methyloxetaneYield 87%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

In a manner similar to the that of Example B14, a mixture of 3-bromomethyl-3-methyloxetane (468 g, 2.84 mol), 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctan-1-ol (1032 g, 2.58 mol), tetrabutylammonium bromide (41.5 g), potassium hydroxide (208 g, 3.23 mol), and water (1680 ml) was heated under reflux for 3 hours. GLC analysis revealed complete consumption of starting materials. The reaction mixture was diluted with water, worked-up in the usual manner, and distilled under reduced pressure to give 1,085 g of 15-FOX, representing an overall yield of 87%; bp 82° C./0.1 mm-Hg. The distilled material was >99% pure as indicated by GLC and was used in subsequent polymerization reactions.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customconsumption of starting materials
  4. additionThe reaction mixture was diluted with water
  5. distillationdistilled under reduced pressure
  6. customto give 1,085 g of 15-FOX,
  7. customwas used in subsequent polymerization reactions

Sources & evidence

ORD record
ord-a299b5ee5b6f418d8013c541bce79efe
Source dataset
uspto-grants-2002_04
Patent number
US06380351B1

Reaction notes

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