Allyl bromide → 1,3-Dinitro-5-{[(prop-2-en-1-yl)oxy]methyl}benzene

Participants

Reaction Steps

20.0 g (101 mmol) of 3,5-dinitrobenzyl alcohol, 22 ml (254 mmol) of allyl bromide and 2.0 g (5.89 g) of tetrabutylamonium hydrogensulfate were dissolved in 100 ml of tetrahydrofuran, and a solution of 8.0 g (200 mmol) of sodium hydroxide as dissolved in 16 ml of water was added thereto and stirred overnight at room temperature. The reaction solution was extracted with diethyl ether and the organic phase was taken out and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product, which was then purified by column chromatography with silica gel (using a developer of chloroform/hexane=1/l). As a result, 19.1 g of 3,5-dinitrobenzyl allyl ether having a structural formula of: ##STR32## was obtained as a yellow oil. Yield: 80%. The product was identified to have the above-mentioned structure by the following IR spectrum, 1H-NMR spectrum and elementary analysis.

Provenance & Evidence