Ethanol → 4-Chloro-2-(propan-2-yl)pent-4-enoic acid

Participants

Reaction Steps

The ethyl 4-chloro-2-isopropyl-4-pentenoate (8.0 g, 0.039 mol) was refluxed for 20 hrs. in 15 ml of water and 15 ml of ethanol containing 4.8 g (0.12 mol) of sodium hydroxide. Most of the ethanol was removed on the rotary evaporator and the residue taken up in 100 ml of water. The aqueous solution was extracted with two 50 ml portions of ether, then acidified with conc. HCl. The acidified mixture was extracted twice with 100 ml of ether. The ether was washed with water, dried (MgSO4), and removed to leave 4.83 g (70% yield) of a light yellow oil.

Provenance & Evidence