Hydrochloric Acid → 3,3-Diethoxypropanoic acid

Temperature

110 °C

To a solution of ethyl 3,3-diethoxypropanoate (20 g, 105 mmol) in water (80 ml) was added sodium hydroxide (5 g, 125 mmol, 1.2 eq). The resulting solution was stirred for 1 hour at 110° C. in an oil bath and then adjusted to pH 5 with aqueous hydrogen chloride (3N). The crude product was then extracted with tetrahydrofuran (3×80 ml) and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered before being concentrated under vacuum. The crude residue was purified by silica gel chromatography using 3-50% ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated under vacuum to afford 3,3-diethoxypropanoic acid as light yellow oil (12 g, 70%); 1H NMR (300 MHz, DMSO): δ 4.80-4.82 (t, J=5.7 Hz, 1H), 3.41-3.61 (m, 4H), 2.49 (d, J=5.7 Hz, 2H), 1.06-1.24 (m, 6H).

1. extractionThe crude product was then extracted with tetrahydrofuran (3×80 ml)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationbefore being concentrated under vacuum
5. customThe crude residue was purified by silica gel chromatography
6. washto elute
7. concentrationconcentrated under vacuum

ORD record

ord-22babc3aede24279848775ec6d45c008

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2