Toluene → HCID 178420343, compound

Participants

Reaction Conditions

Reaction Steps

To a flask equipped with a Dean-Stark apparatus was added benzylamine (B) (97.3 g, 0.91 mol) and toluene (350 g). The mixture was warmed to 110-115° C. and 3-cyclohexene-1-carboxaldehyde (A) (100 g, 0.91 mol) was added over 1-1.5 h, while azeotropically removing water. After the addition was complete, toluene was distilled (approx. 100 mL) and then the reaction was cooled to 20-30° C. The resulting solution was approximately 40 w/w % (1) in toluene. The solution of (1) in toluene was carried forward without further isolation or purification. Typical assay: 99 area % purity (GC), retention time 15.3 min. 1H NMR (400 MHz, CDCl3) δ 7.78-7.75 (1H, m), 7.37-7.32 (2H, m), 7.30-7.26 (3H, m), 5.75-5.73 (2H, m), 4.62 (2H, s), 2.62-2.52 (1H, m), 2.31-2.23 (1H, m), 2.20-2.11 (3H, m), 2.00-1.93 (1H, m), 1.68-1.58 (1H, m).

Provenance & Evidence