Toluene → HCID 33247581, compound

Participants

Reaction Conditions

Reaction Steps

25 g of 4-tert-butylbenzyl bromide, 50 ml of anhydrous toluene and 3.1 g of sodium hydride as an 80% suspension in oil are added under a nitrogen atmosphere to a three-necked flask on which is mounted a condenser, followed by addition of 21.8 g of diethyl acetamidomalonate. The mixture is heated at 110° C. for 17 hours. After cooling, 15 ml of absolute ethanol, then 15 ml of 50% ethanol and then 50 ml of water are added slowly using a dropping funnel. The organic phase is separated out after settling has taken place and the aqueous phase is washed with 3 times 50 ml of diethyl ether. The organic phases are combined, washed with water and then dried over sodium sulphate. After filtering and concentrating under reduced pressure, the product is crystallized from petroleum ether to give 25 g of diethyl 4-(tert-butyl)benzylacetamidomalonate in the form of a white solid melting at 80° C.

Provenance & Evidence