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An example of an ester formation is the substitution reaction between a carboxylic acid (R−C(=O)−OH) and an alcohol (R'OH), forming an ester (R−C(=O)−O−R'), where R and R′ are organyl groups, or H in the case of esters of formic acid.
Esters of propanoic acid are produced commercially by this method: H 2 C=CH 2 + ROH + CO → CH 3 CH 2 CO 2 R. A preparation of methyl propionate is one illustrative example. H 2 C=CH 2 + CO + CH 3 OH → CH 3 CH 2 CO 2 CH 3. The carbonylation of methanol yields methyl formate, which is the main commercial source of formic acid. The reaction is ...
The reaction can also be accomplished with the help of enzymes, particularly lipases (one example is the lipase E.C.3.1.1.3 [2]). Transesterification : alcohol + ester → different alcohol + different ester
Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.
This method can also be used with primary diazoalkanes, to produce secondary α-diazo ketones. However, there are many limitations. Primary diazoalkanes undergo azo coupling to form azines; thus the reaction conditions must be altered such that acid chloride is added to a solution of diazoalkane and triethylamine at low temperature.
This process is the main industrial method for producing glycerol (C 3 H 5 (OH) 3). Some soap-makers leave the glycerol in the soap. Others precipitate the soap by salting it out with sodium chloride. Skeletal formula of stearin, a triglyceride that is converted by saponification with sodium hydroxide into glycerol and sodium stearate.
Examples of this [contradictory] include the common undergraduate organic lab experiment involving the acetylation of salicylic acid to yield aspirin. Fischer esterification is primarily a thermodynamically-controlled process: because of its slowness, the most stable ester tends to be the major product. This can be a desirable trait if there ...
Ethyl and benzyl esters are easily made thereby, and the reaction is noteworthy in that even the highly hindered tert-butyl alcohol gives very high yields in this synthesis. [8] Levi and Zanetti extended the Knorr synthesis in 1894 to the use of acetylacetone (2,4-pentanedione) in reaction with ethyl 2-oximinoacetoacetate.