Isobutyric Acid → Tetramethylammonium Isobutyrate

Reaction equation

[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[OH-].[CH3:8][N+:9]([CH3:12])([CH3:11])[CH3:10]>>[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:8][N+:9]([CH3:12])([CH3:11])[CH3:10]

Participants

Reactant 2

HCID 6590Isobutyric Acid

HCID 60966Tetramethylammonium hydroxide

Product 1

HCID 21900158Tetramethylammonium Isobutyrate

Procedure

To a 20 L round bottom flask was added isobutyric acid (1300 mL, 14 mol), and an aqueous solution of 25% tetramethylammonium hydroxide (5 L, 14 mol). The water was removed under reduced pressure and azeotroped with toluene (2×2 L) to leave the product (13) as an amber liquid, which was used without further purification.

Workup

customThe water was removed under reduced pressure
customazeotroped with toluene (2×2 L)

Sources & evidence

ORD record: ord-d9bf35d5d3d148af934671ce2361fb16
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566738B2

Reaction notes

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