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Organic Lab Reactions 28 - CONDITIONS OF REARRANGEMENT 23...

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CONDITIONS OF REARRANGEMENT 23 the allylic isomers can be separated by careful distillation, the chlorides are much more useful for synthetic work. The Williamson synthesis, using a sodium phenoxide and allyl bromide in methanol solution, is more rapid than the procedure using acetone and potassium carbonate and gives good results. 16 ' 3B ' **• 66 Aqueous ace- tone also has been used as the reaction medium with allyl bromide and sodium hydroxide; this method likewise is rapid and sometimes leads to better yields than the procedure using potassium carbonate and acetone. 34 Allylation of 2-hydroxy-l,4-naphthoquinone has been car- ried out by treating the silver salt, in benzene, with allyl bromide; 84 some C-alkylation as well as O-alkylation was observed. The extent of C-alkylation as a side reaction in etherification varies; about 1% of allyl 2-allylphenyl ether is formed when phenol is used in the acetone and potassium carbonate method with allyl bromide; * with
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