Sodium Carbonate

Na2CO3

[497-19-8]  · CNa2O3  · Sodium Carbonate  · (MW 105.99)

(widely used base)

Physical Data: mp 851 °C; d 2.532 g cm-3.

Solubility: sol glycerol, water.

Form Supplied in: white powder.

Handling, Storage, and Precautions: moderately toxic; severe irritant; noncombustible; stable; decomposition occurs slowly above 400 °C to give carbon dioxide and sodium oxide; incompatible with strong acids and aluminum; hygroscopic.

Selective Hydrolysis.

Cyanoethylated b-keto esters can be hydrolyzed with aqueous sodium carbonate to the corresponding d-keto nitrile (eq 1).1 The use of sodium hydroxide in this reaction leads to hydrolysis of the nitrile, affording the keto acid.

The selective hydrolysis of esters in the presence of acetyl-protected amines can be achieved with aqueous sodium carbonate (eq 2).2

McFadyen-Stevens Reduction.

The decomposition of sulfonylhydrazines to aldehydes was achieved using sodium carbonate as base. The sulfonylhydrazine was heated in ethylene glycol to 150 °C, and 4-6 equiv of sodium carbonate added. The reaction is complete in approximately 30 s. This reaction has been applied to the formation of aromatic,3 heterocyclic,3 and aliphatic aldehydes (eq 3).4

Carbon-Carbon Bond Forming Reactions.

The reaction of b-keto esters with a,b-unsaturated aldehydes in the presence of sodium carbonate and a phase-transfer catalyst afforded the Michael addition product (eq 4).5 The use of sodium hydroxide in this reaction led to substantial decomposition.

This methodology was used to prepare 3-oxo-5-phenyl-1-cyclohexene from ethyl acetoacetate and cinnamic acid (eq 5).5 Under the same conditions, b-cyano esters and a,b-unsaturated aldehydes undergo Knoevenagel condensation (eq 6).5

Hydrogenation.

Sodium carbonate is an effective acid scavenger for hydrogenations. The hydrogenation of m-nitro-O-benzoylmandelate with Raney Nickel and sodium carbonate in ethanol at 180 °C afforded the ethyl ester of m-aminophenylacetic acid (eq 7).6 Other bases were found to be less effective in removing the benzoic acid, resulting in slow and incomplete reactions. Sodium carbonate is also used in the sodium hydrophosphite hydrogenations of many functional groups.7

Synthesis of Phenyliodonium b-Diketonates.

b-Diketones react with (Diacetoxyiodo)benzene in the presence of sodium carbonate to afford phenyliodonium b-diketonates (eq 8).8 Ozonolysis of the phenyliodonium b-diketonates provides an efficient synthesis of triketones.

Other Applications.

Sodium carbonate is used in the alkylation of amines,9 debromination,10 hydrolysis,11 imidazoline synthesis,12 as a buffer,13 and a neutralization agent.14

Related Reagents.

Barium Hydroxide; Cadmium Carbonate; Calcium Carbonate; Cesium Carbonate; Lithium Carbonate; Potassium Carbonate; Potassium Hydroxide; Sodium Hydroxide.


1. Levine, R.; Yoho, C. JACS 1952, 74, 5597.
2. Hill, J. T.; Dunn, F. W. JOC 1965, 30, 1321.
3. Mosettig, E. OR 1954, 8, 232.
4. Sprecher, M.; Feldkimel, M.; Wilchek, M. JOC 1961, 26, 3664.
5. Kryshtal, G. V.; Kulganek, V. V.; Kucherov, V. F.; Yanovskaya, L. A. S 1979, 107.
6. Cronyn, M. W. JOC 1949, 14, 1013.
7. For examples, see: Boyer, S. K.; Bach, J.; McKenna, J.; Jagdmann, E. JOC 1985, 50, 3408.
8. Lick, C.; Schank, K. S 1983, 392.
9. Hu, M. W.; Singh, P.; Ullman, E. F. JOC 1980, 45, 1711.
10. Wolinsky, J.; Erickson, K. L. JOC 1965, 30, 2208.
11. Brown, J.; Brown, R. CJC 1955, 33, 1819.
12. Jung, S.-H.; Kohn, H. JACS 1985, 107, 2931.
13. Emmons, W. D.; Pagano, A. S. JACS 1955, 77, 89.
14. For examples, see: Izumi, Y.; Okada, H.; Matsuda, I. CL 1983, 97; Obrecht, R.; Hermann, R.; Ugi, I. S 1985, 400.

Roger Harrington

Giba-Geigy, Summit, NJ, USA



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