15597ch23_409-42211/7/0516:45Pag0420 EQA 420.chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATON CCHCH.CCH CO2CH2CH3 HCCH.CH.CCH:oLo4了》N-C人 Aldol Cyclohexanone CH.CCH,+CH-0CH.CCH.CH.O CHCCH-CH CO.CH-CH: is-Cyclohexanone 43. CH3O HO
H H Dehydration H product CH3O O O H CH3O Variation of Friedel-Crafts HO
CH3O O H HO (Enol as nucleophile) CH3O O O OH H HO H2O Acid-catalyzed dehydration H CH3O O O H Acid-catalyzed aldol condensation O CH3 CH3O O O Michael addition O HCCH2CO2CH2CH3 CO2CH2CH3 O HCCHCH2CH2CCH3 1. NaOCH O O 2CH3 2. CH3COCH CH2 Same steps as above From above Michael O CH3CCH3 CH2 O CH3CCH CH2 O CH3CCH2CH2OH O O NaOH, H2O Aldol H,  HCCH2CH2CCH3 O O NaOH, H2O,  H2, Pd C

Aldol HCCH2CO2CH2CH3 CO2CH2CH3 O HCCHCH2CCH3 1. NaOCH O O 2CH3 2. BrCH2COCH3 H, H2O,  420 • Chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATION 1559T_ch23_409-422 11/7/05 16:45 Page 420