Sodium Hydroxide → (S)-1-Ethyl-2-oxocyclohexanepropanoic Acid

Participants

Reaction Steps

A solution of (S)-1-ethyl-2-oxocyclohexanepropanoic acid methyl ester (3.25 mol, 689 g) in 1.4 L of ethanol was treated with 1.4 L of 2.5M sodium hydroxide. After 15 minutes at room temperature, the ethanol was removed on a rotary evaporator and the aqueous solution was extracted with ether (2×500 mL). It was acidified with 1 L of 6M hydrochloric acid and extracted with 1×1 L and 2×500 mL of ether. The extracts were combined, dried (magnesium sulfate) and concentrated to a yellow oil (605 g, 3.64 mol, 112%) which was used as in the next step.

Provenance & Evidence