Methyl iodide → 2-(4-Iodo-3-methoxyphenyl)-5,5-dimethyl[1,3]dioxane

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (887 mg, 60% dispersion in mineral oil, 22.2 mmol) was added to an ice-cooled solution of 3-hydroxy-4-iodobenzaldehyde (5.00 g, 20.2 mmol) in DMF (20 ml) and stirred at 0° C. for 60 min. Iodomethane (3.15 ml, 22.2 mmol) was added dropwise to the solution of the phenolate, and the reaction mixture was stirred at room temperature for 4 h. The mixture was diluted with ethyl acetate and washed with ice-water and saturated sodium chloride solution. After drying over magnesium sulfate, the organic phase was concentrated under reduced pressure. The residue (6.32 g) was dissolved in toluene (150 ml) and, after addition of neopentyl glycol (2.76 g, 26.5 mmol) and Amberlyst-15 (400 mg), the reaction mixture was heated under reflux with a water trap for 3 h. After filtration, the reaction solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase gradient 10-25% ethyl acetate in dichloromethane). Yield: 6.83 g (77%) of a yellowish oil. MS (API-ES, pos) m/z=349 [M+H]+

Provenance & Evidence