Methanol → HCID 12980054, compound

Participants

Reaction Steps

2,4,6-Trimethylaniline (7.0 mL, 50 mmol, Aldrich) was mixed with isobutyraldehyde (4.5 mL, 50 mmol, Aldrich), methanol (20 mL), and formic acid (1 mL of a 88% aqueous solution, Fisher). The reaction mixture became reddish and was stirred at RT for 4 h. Assay by 1H-NMR showed a 2/1 mixture of product/starting materials. Additional isobutyric aldehyde (4 mL, 44 mmol) was added to the reaction mixture and it was stirred for 12 h. At this point assay by 1H-NMR showed a 5/1 mixture of product/amine. The solvent and excess aldehyde was evaporated, the residue was distilled at reduced pressure collecting three fractions: 1. 53–56° C./27 Pa, 1/1 mixture of product/amine; 2. 56–59° C., 7/1 product/amine; 3. 59–60° C., pure product (2.3 g, 24.3%). 1H NMR (CDCl3) 7.52 (d, 1H; J=4.8 Hz); 6.84 (br s, 2H); 2.70 (d of septets, 1H; J=4.8; 6.9 Hz); 2.26 (s, 3H); 2.05 (s, 6H); 1.22 (d, 6H; J=6.9 Hz).

Provenance & Evidence