Dolbier HW Solutions 361

Dolbier HW Solutions 361 - 2H 2 O H 1...

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17.37 ( a ) Friedel Crafts acylation of benzene with benzoyl chloride is a direct route to benzophenone. ( b ) On analyzing the overall transformation retrosynthetically, we see that the target molecule may be prepared by a Grignard synthesis followed by oxidation of the alcohol formed. In the desired synthesis, benzyl alcohol must f rst be oxidized to benzaldehyde. Reaction of benzaldehyde with the Grignard reagent of bromobenzene followed by oxidation of the resulting secondary alcohol gives benzophenone. ( c ) Hydrolysis of bromodiphenylmethane yields the corresponding alcohol, which can be oxi- dized to benzophenone as in part ( b ). ( d ) The starting material is the dimethyl acetal of benzophenone. All that is required is acid- catalyzed hydrolysis.
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Unformatted text preview: 2H 2 O H 1 Dimethoxydiphenyl-methane C 6 H 5 CC 6 H 5 OCH 3 OCH 3 C 6 H 5 CC 6 H 5 O Benzophenone Water Methanol 1 2CH 3 OH 1 C 6 H 5 CHC 6 H 5 H 2 O Bromodiphenylmethane Diphenylmethanol C 6 H 5 CHC 6 H 5 OH Br oxidize C 6 H 5 CC 6 H 5 O Benzophenone C 6 H 5 MgBr C 6 H 5 CH O 1. diethyl ether 2. H 3 O 1 Benzaldehyde Phenylmagnesium bromide Diphenylmethanol 1 C 6 H 5 CHC 6 H 5 OH PDC CH 2 Cl 2 C 6 H 5 CC 6 H 5 O Benzophenone C 6 H 5 CH 2 OH C 6 H 5 CH O PDC CH 2 Cl 2 Benzyl alcohol Benzaldehyde C 6 H 5 MgBr 1 C 6 H 5 CHC 6 H 5 OH C 6 H 5 CC 6 H 5 O C 6 H 5 CH O Benzoyl chloride Benzene Benzophenone CCl O 1 AlCl 3 C O ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 455...
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