Reaction of Alkenylmagnesium Bromide with Benzaldehyde

Apparatus Chap. I, Fig. 1, 1 l at a later stage of the reaction, the thermometer-outlet combination is replaced with a reflux condenser. 

In order to keep the reaction time as short as possible, a considerable excess of lithium should be used in the preparation of the lithiocycloalkenes. All chloro-cycloalkene can be added in one portion, if the reaction is carried out on a modest scale (0.3-0.5 molar), the reaction can be kept under control by changing the rate of stirring. Wiirtz coupling to C12 or C14 hydrocarbons and/or HC1 elimination (under the influence of lithiocycloalkene) do not occur. 

The bright color of polished silver disappears when the reaction has stopped. 

The lithium should be destroyed immediately by adding a mixture (7 3) of ethanol and water. 

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