4-Methylbenzoyl Chloride → HCID 19095369, compound

Participants

Reaction Steps

2-(2-Bromoethyl)-1,3-dioxolane (44.3 ml) was added dropwise within 15 minutes under argon and while stirring at a maximum 30° C. to a suspension of Rieke magnesium, prepared from 50.8 g of magnesium chloride, in 1600 ml of absolute tetrahydrofuran. The suspension was stirred at room temperature for 15 minutes, cooled to 0° C. and, after the addition of 49.3 g of copper(I) bromide, stirred at 0° C. for 15 minutes. After cooling to -70° C. 38.5 ml of p-toluoyl chloride were added dropwise within 20 minutes. The reaction mixture was stirred at -70° C. for 30 minutes and at room temperature for 2 hours and subsequently hydrolyzed with 1000 ml of saturated ammonium chloride solution while cooling at a maximum 20° C. After the addition of 500 ml of water the mixture was extracted once with 1000 ml of ethyl acetate and twice with 500 ml of ethyl acetate each time. The combined organic extracts were dried over MgSO4 and freed from solvent. 71.0 g of brown oil were chromatographed on 1500 g of silica gel with ethyl acetate/hexane/methylene chloride (1:4:1) as the eluent. 21.8 g (34%) of 3-(1,3-dioxolan-2-yl)-4'-methylpropiophenone were isolated as a yellow-orange oil.

Provenance & Evidence