AcetaldehydeN-tert-Butylimine

Abstract

[7020-80-6] (E) [62058-77-9] C6H13N (MW 99.17) InChI = 1S/C6H13N/c1-5-7-6(2,3)4/h5H,1-4H3/b7-5+ InChIKey = RPVBCVQKDPOMII-FNORWQNLSA-N InChI = 1/C6H13N/c1-5-7-6(2,3)4/h5H,1-4H3/b7-5+ InChIKey = RPVBCVQKDPOMII-FNORWQNLBY (acetaldehyde equivalent; synthesis of α,β-unsaturated aldehydes) Alternate Names: N-ethylidene-1,1-dimethylethylamine; N-(ethylidene)-tert-butylamine; N-ethylidene-2-methyl-2-propaneamine. Physical Data: bp 25–28 °C/95 mmHg; nD19.2 1.4005. Solubility: sol most organic solvents. Form Supplied in: colorless liquid; not commercially available. Analysis of Reagent Purity: 1H NMR; GC. Preparative Methods: condensation of freshly distilled Acetaldehyde with t-Butylamine without solvent.1-4 The way the reactants are mixed is crucial. tert-Butylamine is added dropwise to 1 equiv of the aldehyde at −10 to 0 °C (eq 1). The reaction mixture is further stirred at rt for 10 min after which solid KOH is added (about 10 g per mol). After separation of the water layer, the imine is distilled over KOH using a Vigreux column. It was reported that azeotropic removal of the water, formed during the reaction, with an organic solvent, nonmixable with water, gave good results.5 However, it was found that this procedure with dichloromethane as solvent gave an end product which was always contaminated with the solvent.4 (1) Handling, Storage, and Precautions: very sensitive to hydrolysis; store in closed vessels under an inert atmosphere in the refrigerator. Use of the freshly distilled reagent is recommended. Use in a fume hood.