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Organic Lab Reactions 31

Organic Lab Reactions 31 - 26 THE CLAISEN REARRANGEMENT...

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26 THE CLAISEN REARRANGEMENT allyl 2-carbomethoxy-6-methylphenyl ether (LXXXV) undergoes the para rearrangement when the ester group is saponified with algoholic alkali. 6 A similar rearrangement 'accompanied by loss of carbon dioxide is observed during hydrolysis of LXXXVI. 73 OCH(C 2 H 6 )CH=CH 2 XCO2CH3 CH3O1 COOCH3 LXXXV LXXXVI ' These variations in reactivity are usually not large enough to be of practical importance. The behavior of ethers of hydroxy acids, some of which rearrange at temperatures not far above 100°, has been discussed (p. ID- Experimental Procedures * Preparation of Allyl Phenyl Ether, f A mixture of 188 g. of phenol, 242 g. of allyl bromide, 280 g. of finely ground calcined potassium carbonate, and 300 g. of acetone is refluxed on the steam bath for eight hours. A heavy precipitate of potassium bromide begins to form soon after the refluxing is started. After cooling, water is added; the product is taken up in ether and washed twice with 10% aqueous sodium hydroxide solution. The ether solution is dried over potassium carbon-
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