Sodium Hydroxide → 4-Ethoxybutanoic acid

To an ice cold stirred solution of ethyl 4-ethoxybutanoate (30) (˜1 g) in 10 mL of tetrahydrofuran (THF) was added aqueous NaOH solution (0.62 g in 7 ml of H2O) and stirred at room temperature for 12 h, while monitoring the reaction by TLC. Most of the solvent was evaporated under reduced pressure and the residue was diluted with water (10 mL). The aqueous layer was acidified with 1N HCl solution (PH˜2) and then extracted with ethyl acetate (15 mL×3). The combined organic extracts was dried over anhydrous Na2SO4 and concentrated under vacuum to yield 0.6 g (73.14) of 4-ethoxybutanoic acid as light yellow oil. 1HNMR (400 MHz, CDCl3): δ 1.20 (t, J=9.2 Hz, 3H); 1.87-1.95 (m, 2H); 2.47 (t, J=10 Hz; 2H); 3.48 (q, J=9.2 Hz, 4H).

1. customthe reaction by TLC
2. customMost of the solvent was evaporated under reduced pressure
3. additionthe residue was diluted with water (10 mL)
4. extractionextracted with ethyl acetate (15 mL×3)
5. dry with materialThe combined organic extracts was dried over anhydrous Na2SO4
6. concentrationconcentrated under vacuum

ORD record

ord-3a5326518f024e21aa9627d4d622f96f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238625B2