O-Xylene → HCID 22238068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dimethyl-N-(2-methyl-2-propenyl)benzeneamine (3.77 g, 21.5 mmol) in xylene (35 mL) was added zinc chloride (8.80 g, 64.6 mmol), and the mixture was stirred at 150° C. for 3.5 hours. Heating was stopped, and a solution of sodium acetate (10.6 g, 0.129 mol) in water (30 mL) was carefully added dropwise to the resulting hot mixture. The resulting solution was cooled, the organic layer was separated, and the aqueous layer was extracted with toluene. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 20:1) to obtain 2.91 g of the title compound.

Provenance & Evidence