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One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation of 2-methoxynaphthalene followed by an acetoacetic ester synthesis. The mechanism involves the following steps: Reaction of formaldehyde with HCl to form cation 1, with the positive charge on the carbon: Reaction of cation 1 with 2-methoxynaphthalene at carbon 6 to form intermediate 2, containing a positive charge on the methoxy oxygen: Deprotonation to form Protonation to form oxonium ion 4: Elimination of water to form carbocation 5: Reaction with chloride ion to form alkyl chloride 6: Reaction of ethoxide ion with ethyl acetoacetate to form enolate ion 7: Reaction of enolate 7 with alkyl chloride 5 to form beta-ketoester 8: Ester hydrolysis to form B-ketocarboxylic acid 9: Decarboxylation to form nabumetone. Work out this synthesis on a separate sheet of paper, and then draw the structure of beta-ketocarboxylic acid 9.
One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation of 2-methoxynaphthalene followed by an acetoacetic ester synthesis. The mechanism involves the following steps: Reaction of formaldehyde with HCl to form cation 1, with the positive charge on the carbon: Reaction of cation 1 with 2-methoxynaphthalene at carbon 6 to form intermediate 2, containing a positive charge on the methoxy oxygen: Deprotonation to form Protonation to form oxonium ion 4: Elimination of water to form carbocation 5: Reaction with chloride ion to form alkyl chloride 6: Reaction of ethoxide ion with ethyl acetoacetate to form enolate ion 7: Reaction of enolate 7 with alkyl chloride 5 to form beta-ketoester 8: Ester hydrolysis to form B-ketocarboxylic acid 9: Decarboxylation to form nabumetone. Work out this synthesis on a separate sheet of paper, and then draw the structure of beta-ketocarboxylic acid 9.
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Patrina SchowalterLv2
23 May 2019
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