Ammonium Chloride → HCID 67146635, compound

Participants

Reaction Steps

Iodine (10 mg) was added to a mixture of magnesium (1.20 g) and tetrahydrofuran (50 mL) with vigorous stirring and 2-(4-bromophenyl)-1,3-dioxolane (10.0 g) was added dropwise at room temperature. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hr and a solution of 2,6-dimethylbenzaldehyde (5.0 g) in tetrahydrofuran (20 mL) was added dropwise at 0° C. After the completion of the dropwise addition, the temperature of the reaction mixture was allowed to return to room temperature and the mixture was further stirred for 1 hr. The reaction mixture was poured into saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was purified by silica gel column chromatography. The residue was developed with ethyl acetate-hexane (gradient of 1:9 to 7:3 by volume ratio) to give the title compound (9.10 g, yield 73%) as a yellow oil.

Provenance & Evidence