Ethanol → Cyclopentanecarboxylic acid, 2-hexyl-3-oxo-, ethyl ester

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Reaction Steps

In a 1 L flask, to which is attached a water separator under a reflux condenser, is placed a solution of 20 g of 2-n-hexyl-3-oxocyclopentanecarboxylic acid, 9.5 g of absolute ethanol and 1 g of p-toluenesulphonic acid in 500 ml of benzene. The reaction mixture is refluxed until no more water separates. The reaction mixture is then cooled and washed successively with water and sodium carbonate solution and dried over anhydrous sodium sulphate. The solvent is removed by distillation at atmospheric pressure and the residue is distilled through a short Vigreux column. Ethyl 2-n-hexyl-3-oxocyclopentanecarboxylate is collected at 102° C/0.25 mm, yield 19,5 g (86%), nD20 1.4535.

Provenance & Evidence