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Question & Answer: One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is…..

acetoacetic ester synthesis 6CH2o, HCI Cl MeO Meo 2 Nabumetone 2-methoxynaphthalene 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: 1. Reaction of formaldehyde with HCl to form cation 1, with the positive charge on the carbon; 2. Reaction of cation 1 with 2-methoxynaphthalene at carbon 6 to form intermediate 2, containing a positive charge on the methoxy oxygen; 3. Deprotonation to form 4. Protonation to form oxonium ion 4; 5. Elimination of water to form carbocation 5; 6. Reaction with chloride ion to form alkyl chloride 6; 7. Reaction of ethoxide ion with ethyl acetoacetate to form enolate ion 7; 8. Reaction of enolate 7 with alkyl chloride 5 to form β-ketoester 8; 9. Ester hydrolysis to form B-ketocarboxylic acid 9; 10. Decarboxylation to form nabumetone. primary alcohol 3; work out this synthesis on a separate sheet of paper, and then draw the structure of β-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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