Acetone → 6-Bromo-2,2-dimethyl-4H-benzo[d][1,3]dioxine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.0 g (24.63 mmol) 3-bromo-6-hydroxybenzyl alcohol in 30 ml acetone cooled to 0° C., a solution of 1.15 g (8.62 mmol) AlCl3 in 20 ml Et2O is added dropwise. The resulting mixture is allowed to stand at room temperature for 1 hr, after which time it is cooled to 0° C. and 50 ml of a 10% NaOH aqueous solution previously cooled to 5° C. is added thereto. The separated Et2O phase is washed twice with 20 ml H2O, dried on anhydrous Na2SO4, evaporated to dryness and distilled under reduce pressure to yield 4.85 g (81%) 2,2-dimethyl-6-bromobenzo-1,3-dioxane as an oil.

Provenance & Evidence