Dolbier HW Solutions 394

Dolbier HW Solutions 394 - propenal CH 3 CCH 2 OH C 6 H 5 CH

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18.31 ( a ) By realizing that the primary alcohol function of the target molecule can be introduced by re- duction of an aldehyde, it can be seen that the required carbon skeleton is the same as that of the aldol addition product of 2-methylpropanal. The synthetic sequence is The starting aldehyde is prepared by oxidation of 2-methyl-1-propanol. ( b ) Retrosynthetic analysis of the desired product shows that the carbon skeleton can be con- structed by a mixed aldol condensation between benzaldehyde and propanal. The reaction scheme therefore becomes Reduction of the aldehyde to the corresponding primary alcohol gives the desired compound. LiAlH 4 , then H 2 O or NaBH 4 , CH 3 OH CH 3 CCH C 6 H 5 CH O 2-Methyl-3-phenyl-2-
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Unformatted text preview: propenal CH 3 CCH 2 OH C 6 H 5 CH 2-Methyl-3-phenyl-2-propen-1-ol 1 HO 2 CH 3 CCH C 6 H 5 CH O 2-Methyl-3-phenyl-2-propenal CH 3 CH 2 CH O Propanal C 6 H 5 CH O Benzaldehyde CH 3 CCH 2 OH C 6 H 5 CH CH 3 CCH C 6 H 5 CH O C 6 H 5 CH 1 CH 3 CH 2 CH O O PCC CH 2 Cl 2 O (CH 3 ) 2 CHCH 2-Methylpropanal (CH 3 ) 2 CHCH 2 OH 2-Methyl-1-propanol NaBH 4 CH 3 OH NaOH ethanol O (CH 3 ) 2 CHCH 2-Methylpropanal CH 3 CH 3 HO (CH 3 ) 2 CHCHCC H O 3-Hydroxy-2,2,4-trimethylpentanal CH 3 CH 3 HO (CH 3 ) 2 CHCHCCH 2 OH 2,2,4-Trimethyl-1,3-pentanediol O 2(CH 3 ) 2 CHCH CH 3 CH 3 HO (CH 3 ) 2 CHCHCCH 2 OH CH 3 CH 3 HO (CH 3 ) 2 CHCH CC H O 488 ENOLS AND ENOLATES...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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