Pyridine → Methyl 2,2,3,3,4,4,4-heptafluorobutanoate

HRID 2071914Notes

Reaction equation

HRID 2071914 reaction equation
N1C=CC=C[CH:2]=1.[F:7][C:8]([F:19])([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=[O:10]>CO>[F:7][C:8]([F:19])([C:12]([F:17])([F:18])[C:13]([F:14])([F:15])[F:16])[C:9]([O:11][CH3:2])=[O:10]

Participants

4

Reactant 2

HCID 1049PyridineHCID 9777Heptafluorobutyric acid

Product 1

HCID 67741Methyl 2,2,3,3,4,4,4-heptafluorobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cationic fluorochemical surfactants useful as antistatic agents and lubricants for polymeric shapes are prepared from 2,2,3,4,4,4-hexafluorobutanol or perfluorobutyric acid. Hexafluorobutanol is reacted with bromoundecanoic acid to obtain a bromoester which is then reacted with pyridine to obtain a cationic surfactant. Perfluorobutyric acid is esterified with methanol to obtain methyl perfluorobutyrate which is then reacted with dimethylaminopropylamine to obtain an amino-amide which is then reacted with hydrogen peroxide to obtain the N-oxide derivative which is neutralized with glycolic acid to obtain a cationic surfactant, a salt of the N-oxide derivative.

Workup

  1. customto obtain a cationic surfactant

Sources & evidence

ORD record
ord-721a42c651104617a3382fbcfc6292aa
Source dataset
uspto-grants-1977_09
Patent number
US04049668

Reaction notes

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