Methyl 2,2,3,3,4,4,4-heptafluorobutanoate → Sodium perfluorobutanoate

HRID 3935

Reaction equation

HRID 3935 reaction equation
[F:1][C:2]([F:14])([C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]([O:5]C)=[O:4].C[Si](C)(C)[O-].[Na+:20]>CCOCC>[F:1][C:2]([F:14])([C:7]([F:12])([F:13])[C:8]([F:9])([F:10])[F:11])[C:3]([O-:5])=[O:4].[Na+:20]

Participants

4

Reactant 2

HCID 67741Methyl 2,2,3,3,4,4,4-heptafluorobutanoateHCID 23672319Sodium trimethylsilanolate

Product 1

HCID 23678859Sodium perfluorobutanoateYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl perfluorobutyrate (12.81 g, 56 mmol) was added dropwise to a stirred solution of sodium trimethylsilanolate (6.3 g, 56 mmol) in dry ether (300 mL) at room temperature under nitrogen. The reaction mixture was stirred overnight. The solid was filtered under nitrogen, washed with dry ether, and dried under a stream of nitrogen to afford sodium perfluorobutyrate (11.1 g, 84% yield) as a white solid: 19F NMR (D2O) δ -79.6 (t, J=8 Hz, CF3 --, 3F), -117.2 (q, J=8 Hz, CF3CF2CF2 --, 2F), -126.2 ppm (s, CF3CF2 --, 2F). Anal. Calcd. for C4F7NaO2 : C, 20.36; F, 56.35; Na, 9.74. Found: C, 20.84, 20.61, 20.58; F, 56.68, 53.24; Na, 9.89, 9.65.

Workup

  1. filtrationThe solid was filtered under nitrogen
  2. washwashed with dry ether
  3. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-fdcb81caf14240578e9ddd54ada0a201
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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