3-Chloro-1-butene → 1-(1-Methyl-2-propenyloxy)-5-methyl-2-nitrobenzene

Participants

Reaction Steps

24 g of sodium hydride was added in portions to a stirred mixture of 153 g of 5-methyl-2-nitrophenol and 500 ml of DMSO. Then 135.7 g of 3-chloro-1-butene was added drop-by-drop (over 5 minutes) to the stirred mixture, which then was stirred at reflux (79°-81° C.) for 24 hours. Then the mixture was made basic with 50% aqueous sodium hydroxide, poured over ice water and extracted with methylene chloride. The extract was washed with cold water, dried (MgSO4), filtered and stripped of solvent, to give 1-(1-methyl-2-propenyloxy)-5-methyl-2-nitrobenzene (1A), as a dark-colored syrup.

Provenance & Evidence