Dolbier HW Solutions 501

Dolbier HW - 2 CH 3 2 C 6 H 5 CH 2 CH 2 COOH 1 C 6 H 5 CH 2 CH 2 COH O C 6 H 5 CH 2 X CH 2 COH O 1 2 CH 3 CCH 2 COCH 2 CH 3 C 6 H 5 CH 2 Br NaOCH 2

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Formation of the amide completes the synthesis of capsaicin. 21.25 ( a ) First write out the structure of 4-phenyl-2-butanone and identify the synthon that is derived from ethyl acetoacetate. Therefore carry out the acetoacetic ester synthesis using a benzyl halide as the alkylating agent. ( b ) Identify the synthon in 3-phenylpropanoic acid that is derived from malonic ester by discon- necting the molecule at its a -carbon atom. Here, as in part ( a ), a benzyl halide is the required alkylating agent. CH 2 (COOCH 2 CH 3 ) 2 NaOCH 2 CH 3 ethanol Benzyl bromide Diethyl malonate Diethyl benzylmalonate 3-Phenylpropanoic acid 1. HO 2 , H 2 O 2. H 1 3. heat C 6 H 5 CH 2 Br C 6 H 5 CH 2 CH(COOCH
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Unformatted text preview: 2 CH 3 ) 2 C 6 H 5 CH 2 CH 2 COOH 1 C 6 H 5 CH 2 CH 2 COH O C 6 H 5 CH 2 X CH 2 COH O 1 2 CH 3 CCH 2 COCH 2 CH 3 C 6 H 5 CH 2 Br NaOCH 2 CH 3 ethanol CH 3 CCHCOCH 2 CH 3 O O O O CH 2 C 6 H 5 Ethyl acetoacetate Benzyl bromide CH 3 CCH 2 CH 2 C 6 H 5 O 4-Phenyl-2-butanone 1. HO 2 , H 2 O 2. H 1 3. heat 1 Ethyl 2-benzyl-3-oxobutanoate C 6 H 5 CH 2 OH C 6 H 5 CH 2 Br HBr or PBr 3 Benzyl alcohol Benzyl bromide C 6 H 5 CH 2 C 6 H 5 CH 2 X CH 2 CCH 3 O CH 2 CCH 3 O 1 2 SOCl 2 COH O CCl O CNHCH 2 OCH 3 OH O HO CH 2 NH 2 CH 3 O Capsaicin (C 18 H 27 NO 3 ) ESTER ENOLATES 595...
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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