154 Preparation of Alcohols from Epoxides i ia (cH),c—cncH. creer, A (cy), ccricH,cH,cHcH, 6 Mey epen 2 one 6 Mey Shepen 201 00%) 15.3. PREPARATION OF ALCOHOLS BY REDUCTION OF CARBOXYLIC ACIDS AND ESTERS Carboxylic acids are exceedingly difficult to reduce, Acetic acid, for example, is often used as a solvent in catalytic hydrogenations because it is inert under the reaction con- ditions. A very powerful reducing agent is required to convert a carboxylic acid to a pri- ‘mary alcohol, Lithium aluminum hydride is that reducing agent i lon aes, pea cate aid Pony at Deco MeN, DS. you popinctyi celtic (8%) cid Sodium borohydride is not nearly as potent a hydride donor as lithium aluminum hydride and does not reduce carboxylic acids. Esters are more easily reduced than carboxylic acids, Two alcohols are formed from each ester molecule, The acyl group of the ester is cleaved, giving a primary alcohol I) RCOR’'—> RCH,OH + ROH Eset Primary alcohol Alcobel Lithium aluminum hydride is the reagent of choice for reducing esters to alcohols ° I 1_LiAIMy diethyl eter, Buby benzoate Benzyl alcohol (90%) Bthanol PROBLEM 15.3. Give the structure of an ester that will yield a mixture contai aluminum hydride, Sodium borohydride reduces esters, but the reaction is too slow to be useful Hydrogenation of esters requires a special catalyst and extremely high pressures and tem- peratures; itis used in industrial setings but rarely in the laboratory. 15.4 PREPARATION OF ALCOHOLS FROM EPOXIDES ‘Although the chemical reactions of epoxides will not be covered in detail until the fol- lowing chapter, we shall introduce their use in the synthesis of alcohols here, ‘atavichyrogenation frould net be autable for Shir ransformation, becouse Hy adds to carbon-carbon ble bonds faster than