Choline → Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, 2-ethylhexanoate (1:1)

Reaction equation

[OH-].[OH:2][CH2:3][CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].[CH2:9]([CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12]([OH:14])=[O:13])[CH3:10].OCC[N+](C)(C)C.C(OC(=O)CCCCC)C>>[CH3:18][CH2:17][CH2:16][CH2:15][CH:11]([C:12]([O-:14])=[O:13])[CH2:9][CH3:10].[CH3:6][N+:5]([CH2:4][CH2:3][OH:2])([CH3:8])[CH3:7]

Participants

Reactant 4

HCID 305Choline

HCID 86972-Ethylhexanoic Acid

HCID 31255Choline, hydroxide

HCID 31265Ethyl hexanoate

Product 1

HCID 111386Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, 2-ethylhexanoate (1:1)

Procedure

272.13 g of a 40% solution of choline hydroxide and 145.73 g of 2-ethylhexanoic acid were stirred vigorously for 30 min at RT in a glass flask with reflux condenser, heatable oil bath, mechanical stirrer and internal thermometer. Water and methanol were distilled off in a rotary evaporator at 30-45° C. under a vacuum increased gradually to 20 mbar. The product was then taken up in n-hexane and re-evaporated in the rotary evaporator and dried at 0.1 mbar and 40° C. for 2 h, giving a slightly colored, viscous liquid whose 1H-NMR spectrum showed equimolar ratios of choline and ethylhexanoate, but only a weak signal in the region of aliphatic carboxylic acids.