2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 86724119, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methylbenzaldehyde (1.99 g, 10.00 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (2.16 g, 15.0 mmol) in water (20 mL) and 1-4-dioxane (2 mL) was heated at about 75° C. for about 2 h. Additional 2,2-dimethyl-1,3-dioxane-4,6-dione (0.72 g, 5.0 mmol) was added and heating at about 75° C. was continued for about 2 h. The reaction was cooled to rt and solids were filtered off and rinsed with water (25 mL). The resulting solid was air dried on the funnel and then triturated with Et2O (about 20 mL) and filtered. The product was dried overnight in the vacuum oven at about 50° C. to yield 5-(4-bromo-2-methylbenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.75 g, 8.46 mmol, 85%) as a pale yellow solid: LC-MS (Table 1, Method g) Rt=2.43 min, m/z 341/343 (M−H+NH3)−; 1H NMR (400 MHz, DMSO-d6) δ 8.49 (s, 1H), 7.58 (d, J=1.8 Hz, 1H), 7.51-7.42 (m, 2H), 2.33 (s, 3H), 1.77 (s, 6H).

Provenance & Evidence