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21.6
TheAcetoaceticEsterSynthesis
AcetoaceticEsterAcetoaceticesterisanothernameforethylacetoacetate.Theacetoaceticestersynthesisusesacetoaceticesterasareactantforthepreparationofketones.CCCOCH2CH3HHOOH3C
DeprotonationofEthylAcetoacetateCH3CH2OCCCOCH2CH3HHOOH3C+–pKa~11 Ethylacetoacetatecanbeconvertedreadilytoitsanionwithbasessuchassodiumethoxide.
DeprotonationofEthylAcetoacetatepKa~16CH3CH2OCCCOCH2CH3HHOOH3C+CCCOCH2CH3HOO??–H3C+CH3CH2OH–pKa~11 Ethylacetoacetatecanbeconvertedreadilytoitsanionwithbasessuchassodiumethoxide.K~105
AlkylationofEthylAcetoacetateCCCOCH2CH3HOO??–H3CTheanionofethylacetoacetatecanbealkylatedusinganalkylhalide(SN2:primaryandsecondaryalkylhalidesworkbest;tertiaryalkylhalidesundergoelimination).RX
AlkylationofEthylAcetoacetateCCCOCH2CH3HOO??–H3CTheanionofethylacetoacetatecanbealkylatedusinganalkylhalide(SN2:primaryandsecondaryalkylhalidesworkbest;tertiaryalkylhalidesundergoelimination).RXCCCOCH2CH3HOOH3CR
ConversiontoKetoneSaponificationandacidificationconvertthealkylatedderivativetothecorrespondingb-ketoacid.Theb-ketoacidthenundergoesdecarboxylationtoformaketone.CCCOCH2CH3HOOH3CRCCCOHHOOH3CR1.HO–,H2O2.H+
ConversiontoKetoneSaponificationandacidificationconvertthealkylatedderivativetothecorrespondingb-ketoacid.Theb-ketoacidthenundergoesdecarboxylationtoformaketone.CCCOHHOOH3CRCCH2RCO2OH3C+
Example1.NaOCH2CH32.CH3CH2CH2CH2BrOOCH3CCH2COCH2CH3
Example(70%)1.NaOCH2CH32.CH3CH2CH2CH2BrOOCH3CCH2COCH2CH3OOCH3CCHCOCH2CH3CH2CH2CH2CH3
Example(60%)OCH3CCH2CH2CH2CH2CH31.NaOH,H2O2.H+3.heat,-CO2OOCH3CCHCOCH2CH3CH2CH2CH2CH3
Example:DialkylationOOCH3CCHCOCH2CH3CH2CHCH2
Example:Dialkylation1.NaOCH2CH32.CH3CH2IOOCH3CCHCOCH2CH3CH2CHCH2OCH3CCCOCH2CH3CH2CHCH2OCH3CH2(75%)
1.NaOH,H2O2.H+3.heat,-CO2OCH3CCCOCH2CH3CH2CHCH2OCH3CH2Example:DialkylationCH3CCHCH2CHCH2OCH3CH2
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