Hydrochloric Acid → 3,3-Diethoxypropanoic acid

Participants

Reaction Conditions

Reaction Steps

Small pellets of solid NaOH (5.00 g, 125 mmol) were slowly added to a mixture of ethyl 3,3-diethoxypropionate (19.02 g, 100 mmol) and water (35 mL). As the NaOH dissolved the mixture became a homogeneous solution. The solution was heated to 110° C. for 30 min. The reaction was allowed to cool to ambient temperature and then chilled with an ice-water bath. The solution was acidified with drop-wise addition of concentrated aqueous HCl (9.37 mL, 113 mmol). The solution was allowed to warm to ambient temperature and then extracted with dichloromethane (4×15 mL). The combined organic extracts were washed with brine (15 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to yield 15.11 g of 3,3-diethoxypropionic acid as a yellow oil.

Provenance & Evidence