Fluorotelomer alcohol 4:2 → HCID 87580551, compound

HRID 2414711Notes

Reaction equation

HRID 2414711 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[F:9][C:10]([F:24])([C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:12][OH:13]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:7][CH2:12][CH2:11][C:10]([F:9])([F:24])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])(=[O:8])[C:2]([CH2:4][C:5]([O:13][CH2:12][CH2:11][C:10]([F:24])([F:9])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19])=[O:6])=[CH2:3]

Participants

5

Reactant 2

HCID 74883Fluorotelomer alcohol 4:2HCID 75110Itaconic Anhydride

Product 1

HCID 87580551HCID 87580551, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

13.5 g (0.12 moles) of itaconic anhydride, 69.8 g (0.26 moles) of 3,3,4,4,5,5,6,6,6-nonafluorohexanol, and 1.14 g (6 millimoles) of p-toluene sulfonic acid first hydrate were heated and refluxed in 500 mL of toluene for 12 hours, while distilling off water which was generated therein. Then, the mixture was cooled to room temperature, to this ethyl acetate was added, and an organic phase was washed with 1 mol/L of sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution to obtain 51.3 g (69% yield) of compound as oil-state compound.

Workup

  1. distillationwhile distilling off water which
  2. additionwas added
  3. washan organic phase was washed with 1 mol/L of sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution

Sources & evidence

ORD record
ord-ff5fff4cb2cf4611b3dbc2ba79290dce
Source dataset
uspto-grants-2004_11
Patent number
US06815152B2

Reaction notes

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