Water → 5,5-Dichloro-3-methyl-2-(propan-2-yl)pent-4-enoic acid

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Reaction Steps

A solution of 23.41 g (0.0925 mol) of ethyl 5,5-dichloro-3-methyl-2-isopropyl-4-pentenoate, 11.10 g (0.278 mol) of sodium hydroxide, 40 ml of water, and 40 ml of ethanol was refluxed for 3 days under N2, the solvent was concentrated on the rotary evaporator, the residue taken up in 300 ml of water and extracted 2× with ether. The aqueous layer was acidified with conc. HCl, then extracted 3× with 150 ml of ether. The combined ether extracts were washed with water, dried (MgSO4), and stripped to give 17.09 g (82% yield) of the desired acid.

Provenance & Evidence