Neopentyl glycol → HCID 14403835, compound

Participants

Reaction Steps

A mixture of 1.00 g (4.19 mmol) of (E)-3-(2-bromo-4,6-dimethylphenyl)-2-propenal, 1.32 g (12.6 mmol) of 2,2-dimethyl-1,3-propanediol and a catalytic amount (65 mg) of p-toluenesulfonic acid monohydrate in 100 mL of dry benzene was heated at reflux in a Dean-Stark apparatus for 2 hours. The solution was washed with 1N sodium hydroxide, water (3 times), and the solvent removed under reduced pressure to give 1.32 g (97%) of (E)-2-[2-(2-bromo-4,6-dimethylphenyl)ethenyl]-5,5-dimethyl-1,3-dioxane as a white crystalline material. Purification by HPLC (70% CH2Cl2 -Hexane) gave an analytically pure sample: mp 54°-56° C.; IR (KBr) 2960, 2860, 1670 and 1610 cm-1 ; NMR (CDCl3) δ 0.77 (3H, s), 1.25 (3H, s), 2.28 (3H, s), 2.37 (3H, s), 3.58 (2 H, d, J=12 Hz), 3.74 (2H, d, J=12 Hz), 5.09 (1H, d, J=6 Hz), 5.90 (1H, dd, J=6, 15 Hz), 6.78 (1H, d, J=15 Hz), 6.96 (1H, s), 7.30 (1H, s).

Provenance & Evidence