Description
Trimethylacetaldehyde (also known as Pivaldehyde) is the trimethyl
form of acetaldehyde. It is an aldehyde with a sterically bulky R
group, the tertiary-butyl group being attached to the carbonyl,
>C=O. It is a useful reagent in organic synthesis, pharmaceuticals,
agrochemicals and dyestuff. It is useful in streoselective synthesis
application as well as in aldol condensation reactions. As a
derivative of acetaldehyde, trimethyl acetaldehyde can be used for
the production of acetate. It can also be used as the precursor for
manufacturing of pyridine derivatives, pentaerythritol, and
crotonaldehyde.
Chemical Properties
Clear colorless liquid
Uses
Trimethylacetaldehyde is used as a stereoselective synthesis application. It is also used as a building block used in aldol condensation reactions. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Uses
Commonly used building block in aldol condensation reactions.
Definition
ChEBI: 2,2-dimethylpropanal is a member of the class of propanals that is propanal substituted by two methyl groups at position 2. It is a member of propanals and a 2-methyl-branched fatty aldehyde.
Application
Pivaldehyde is a hazardous by-product released from engine exhaust and is often used as a raw material for organic synthesis or as a reagent in chemical reactions. It can be copolymerised with aldehyde anions, such as acrolein, to prepare unsaturated polyacetals, or a TBPB initiated decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde leads to tert-butyl containing quinolone-2,4(1H,3H)-diones by formation of both C(sp
3)–C(sp
3) and C(s
p3)–C(sp
2) bonds. As well as probing the absolute rate constants of its autoxidation, etc
[1-3].
Synthesis
Pivaloyl chloride was used as raw material, palladium-carbon poisoned by quinoline-S was used as catalyst, and the reduction reaction was carried out with hydrogen in a solvent to which an acid-binding agent was added, and the reaction solution was sequentially filtered, washed, extracted, dried and distilled to obtain pivaloyl aldehyde.
References
[1] A. LAPENA R. S J L Mateo. Anionic copolymerization of acrolein with aldehydes. III[J]. Journal of Polymer Science: Polymer Symposia, 1973, 42 1: 311-319. DOI:
10.1002/polc.5070420133.
[2] CUI ZHANG. Decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde: Access to tert-butyl containing quinolone-2,4(1H,3H)-diones[J]. Tetrahedron, 2022. DOI:
10.1016/j.tet.2021.132547.
[3] G. ZAIKOV K. I J Howard. Absolute rate constants for hydrocarbon autoxidation. XIII. Aldehydes: photo-oxidation, co-oxidation, and inhibition[J]. Canadian Journal of Chemistry, 1969. DOI:
10.1139/V69-500.
[4] Ho, Tse Lok, et al. Pivaldehyde. Fieser and Fieser's Reagents for Organic Synthesis. John Wiley & Sons, Inc. 2006.
[5] https://en.wikipedia.org/wiki/Acetaldehyde#Uses
[6] https://en.wikipedia.org/wiki/Pivaldehyde
[7] https://www.alfa.com/en/catalog/A15013/
[8] GEORGE A. OLAH. Acid-Catalyzed Isomerization of Pivalaldehyde to Methyl Isopropyl Ketone via a Reactive Protosolvated Carboxonium Ion Intermediate[J]. Journal of the American Chemical Society, 2001, 123 47: 11556-11561. DOI:
10.1021/ja011253a.
[9] O. SUGIMOTO. Preparation and reaction of quinolinyl (or pyridinyl)phosphonium salts with base and pivalaldehyde[J]. Heterocycles, 2011, 56 1: 837-847. DOI:
10.3987/COM-11-12154.
[10] SUNG MAN PARK Chan H K Yu Ran Lee. Conformational Structures of Neutral and Cationic Pivaldehyde Revealed by IR-Resonant VUV-MATI Mass Spectroscopy.[J]. International Journal of Molecular Sciences, 2022, 23 23. DOI:
10.3390/ijms232314777.
