215F07-notes-10-10-07 - Chem 215 F07 Notes Dr Masato...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 3. Date: October 10, 2007 Chapter 15: Carboxylic Acids and Their Derivatives. VI. Ester Formation: Some of Other Commonly Used Methods (1) From carboxylic acids a. With diazomethane O H O benzoic acid H 2 C N N HOCH 3 (solvent) O CH 3 O H 2 C N N O O H 3 C N N N N (gas) ester [methyl benzoate] (diazomethane) S N 2! b. With base and reactive alkyl iodide [usually CH 3 I or CH 3 CH 2 I] or sulfate [usually (CH 3 ) 2 SO 4 (dimethyl sulfate) or CH 3 CH 2 SO 4 (diethyl sulfate)] + OH HO HO O O H H H H H OH HO HO O O H H H H OH HO HO O O CH 3 H H H H CH 3 I NaHCO 3 (weak base) DMA* (solvent) N , N -dimethylacetamide: polar aprotic solvent that can dissolve NaHCO 3 Na H 3 C I NaI S N 2! N(CH 3 ) 2 O * 91% -------------------------------------------------------------------------------------------------- O H O N O O O S O O O (diethyl sulfate) N , N -dimethylformamide: polar aprotic solvent that can dissolve Na 2 CO 3 Na 2 CO 3 (weak base) DMF* (solvent) O CH 2 CH 3 O N O O H N(CH 3 ) 2 O * 88% (2) With Acid Anhydrides and Acid Chlorides from Alcohols OH H 3 CO O H 3 CO CH 3 O H 3 C O CH 3 O O [ Ac 2 O ]
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