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Acrolein diethyl acetal is a reagent used for the synthesis of a variety of compounds, including cinnamaldehydes.
Gianfranco Battistuzzi; Sandro Cacchi and Giancarlo Fabrizi. An Efficient Palladium-Catalyzed Synthesis of Cinnamaldehydes from Acrolein Diethyl Acetal and Aryl Iodides and Bromides. Org. Lett. 2003, 5 (5), 777-780.
Carmen Nájera; Luis Botella. Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle. Tetrahedron. 2005, 61 (41), 9688-9695.
Protected acrolein equivalent. Reacts with Grignard reagents (CuBr catalysis) to give predominantly (Z)-enol ethers which can be hydrolyzed to 3-substituted propionaldehydes: Tetrahedron Lett., 3833 (1975). The (E)-enol ether is formed selectively with a Ni(II)-phosphine catalyst: Chem. Lett., 351 (1985).
Heck coupling (see Palladium(II) acetate, 10516) occurs with aryl or vinyl bromides in the presence of morpholine or piperidine: J. Org. Chem., 46, 1061 (1981); J. Chem. Soc., Perkin 1, 2597 (1987):
In the presence of acid, generates the ethoxyallyl cation which is a powerful dienophile, undergoing Diels-Alder reactions at low temperatures: J. Am. Chem. Soc., 109, 2182 (1987).
Hazard Statements: H225-H319
Highly flammable liquid and vapour. Causes serious eye irritation.
Precautionary Statements: P210-P280a-P240-P303+P361+P353-P305+P351+P338-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.