Reaction #554628

Reaction equation

ethyl 3,3-diethoxypropanoate

NaOH

HCl

EtOAc

→

3,3-diethoxypropanoic acid

Yield 96.0%

Solvents

water

Conditions

Workup

1. 1
   Extractionthe aqueous layer was extracted with CH2Cl2
2. 2
   DryingThe combined organic layers were dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated

Procedure

A solution of ethyl 3,3-diethoxypropanoate (4.2 g, 22.0 mmol, 1 eq) and NaOH (1.1 g, 28 mmol, 1.3 eq) in water (8 mL) was heated in a 110° C. oil bath for 1.25 h. The reaction was then cooled to 0° C. and was stirred with concentrated HCl (2.3 mL) and EtOAc (20 mL). The organic layer was saved, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and evaporated to afford 3,3-diethoxypropanoic acid (3.41 g, 96% yield) as an orange oil, which was used in the next step without any further purification.

Source