Paraldehyde → HCID 14618374, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(1,1-dimethylethyl)-6-methyl-3-(1-methylethyl)-2-hydroxy-benzenemethanol (7.09 g, 0.03 mol), p-dioxane (150 mL), paraldehyde (13.2 g, 0.3 mol) and p-toluenesulfonic acid monohydrate (0.57 g, 0.003 mol) was heated at reflux for 1.5 hours. The mixture was cooled to 25° C., poured onto water (100 mL) and extracted with hexane (3×50 mL). The extracts were washed with saturated sodium bicarbonate solution (2×50 mL), water (4×50 mL), brine (50 mL) and dried (Na2SO4). Evaporation of solvents and distillation of the residue gave 5.56 g (71% yield, GLC purity 99%) of 2,5-dimethyl-6-(1,1-dimethylethyl)-8-(1-methylethyl)-4H-1,3-benzodioxin, bp 110°-120° C., 0.5 mm; 1H-NMR (CDCl3)δ 1.20 (6H, d, J=7 Hz), 1.40 (9H, s), 1.54 (3H, d, J=5 Hz), 2.20 (3 H, s), 2.9-3.5 (1H, m), 4.80 (2H, s), 5.07 (1H, q, J=5 Hz), 7.10 (1H, s); IR (film)νmax 2940, 1585, 1410 cm-1 ; MS m/e 262, 218, 203, 175, 161; UVλmax (ethanol) 225 (ε=6960), 281 (ε=2040).

Provenance & Evidence