Sodium Iodide → HCID 591785, compound

Participants

Reaction Conditions

Reaction Steps

For example, a solution of 2-carboethoxy-cycloheptanone (I) (92.2 g, 0.5 mole) in toluene (1.6 l) is treated with sodium iodide (1 g) and 60% sodium hydride in mineral oil (23.3 g, 0.58 mole). The mixture is heated at 110° C. until hydrogen gas evolution drops off. Ethyl bromoacetate (98.0 g, 0.58 mole) is added dropwise and the mixture is warmed to 65° C. for 18 hours. The mixture is cooled and water (500 ml) is added. The layers are separated and the aqueous layer is extracted with toluene (2×1 l). The extracts are dried (MgSO4) and filtered. The filtrate is concentrated at reduced pressure and distilled to yield pure 2-carboethoxy-2-carboethoxymethylcycloheptanone (II) with a bp 182°-185° C. at 13 mm.

Provenance & Evidence