Sodium Hydroxide → 5,5-Dibromo-2-(propan-2-yl)pent-4-enoic acid

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Reaction Steps

In a mixture of 7 g of water and 20 g of ethanol were dissolved 1.1 g of sodium hydroxide and 4.6 of the ethyl α-(3.3-dibromoallyl)isovalerate obtained above were added to the above solution. The mixture was stirred at room temperature overnight and, then, refluxed for 3 hours. The reaction mixture was then distilled to remove the ethanol and the residue was made acidic by the addition of dilute hydrochloric acid and extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate and the low-boiling fraction was distilled off. By the above procedure there were obtained 3.7 g of α-(3,3-dibromoallyl)isovaleric acid, the NMR spectrum of which is shown below [yield: 88% based on ethyl α-(3,3-dibromoallyl)isovalerate].

Provenance & Evidence