Sodium Hydroxide → 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Participants

Reaction Steps

1 N NaOH (275 mL, 275 mmol) was added under nitrogen dropwise to a solution of 1,1-cyclopropanedicarboxylic acid diethyl ester (51.3121 g, 275 mmol) in 400 mL of absolute ethanol at room temperature. After the addition, the reaction was allowed to stir at room temperature overnight. The reaction was concentrated under reduced pressure to remove most of the ethanol. The residue was partitioned between water and ether. The aqueous layer was separated, extracted with ether, acidified with 2 N HCl and extracted four times with ether. The combined extracts were dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give a yellow oil. The oil was dissolved in methylene chloride, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1,1-cyclopropanedicarboxylic acid monoethyl ester (39.8275 g, 91%) as a yellow oil.

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