Propiolic Acid Sodium Salt synthesis

Yield:920-38-7 99%

Reaction Conditions:

with sodium hydroxide in methanol at 10 - 20; for 1 h;Darkness;

Steps:

1 Preparation of Sodium Propiolate (2-Na)

Preparation of Sodium Propiolate (2-Na)
Sodium propiolate (2-Na) can be conveniently prepared in nearly quantitative yield by treating propiolic acid with sodium hydroxide in methanol (J. D. Jaufmann, et al., J. Solid State. Chem. 2000, 152, 99-104); however, sodium propiolate is somewhat light sensitive, and thus, the reaction and product isolation should be conducted using appropriate safeguards to avoid light decomposition.
In a darkened hood, ground sodium hydroxide (8.565 g, 0.214 mol) was dissolved in 1 L of methanol in a 2 L round bottom flask.
The solution was cooled to 10° C., and propiolic acid (15.0 g, 0.214 mol) was added with stirring.
The solution was stirred for 1 hour at room temperature after which the solvent was removed by rotary evaporation at a water bath temperature of ≦25° C.
A white solid product, which was dried under high vacuum, was obtained (19.50 g, 99%).
The compound was light sensitive, and thus, stored in the dark. ¹H NMR (CD₃OD): δ 3.36; ¹³C NMR (CD₃OD): δ 160.8 (C=O), 81.8 (H-C≡C), 69.3 (H-C≡C).

References:

US2013/79554,2013,A1 Location in patent:Paragraph 0049