1,2-Dibromoethane → Ethyl 3-(2-bromoethoxy)-2-methylbenzoate

Participants

Reaction Steps

13.6 g (0.2 mol) of sodium methoxide are dissolved in 200 ml of ethanol. 36 g (0.2 mol) of ethyl 3-hydroxy-2-methylbenzoate are then added and the mixture is refluxed for 2 hours. 61.4 g (0.32 mol) of 1,2-dibromoethane are then added dropwise and the mixture is heated to reflux for 20 hours. The cooled reaction mixture is concentrated on a rotary evaporator. The residue is taken up with ethyl acetate and washed 3 times with dilute sodium hydroxide solution. The organic phase is dried and the solvent is distilled off. The useful product is purified by column chromatography. Yield: 14.6 g of oil

Provenance & Evidence