Hydrochloric Acid → 4-(2-Dimethylamino-ethoxy)-benzoic acid

0.69 g (3.09 mmol) of methyl 4-(2-dimethylaminoethoxy)benzoate was dissolved in 15 ml of methanol. 4.64 ml of a 1N sodium hydroxide aqueous solution was added thereto and the mixture was refluxed under heating for 3 hours. After cooling, 4.64 ml of 1N hydrochloric acid was added and the mixture was concentrated to dryness. A chloroform-methanol mixed solution (1:1 (v/v)) was added to the residue. The solution was stirred for a while and filtered with Celite. The solvent was distilled off under reduced pressure to obtain 0.65 g (3.09 mmol) of 4-(2-dimethylaminoethoxy)benzoic acid shown below as a pale yellow solid. ##STR17## Its spectroscopic data are as follows: 1H-NMR (DMSO-d6) δ (ppm): 2.27 (6H, s), 2.71 (2H, t, J=5.6 Hz), 4.14 (2H, t, J=5.8 Hz), 7.01 (2H, d, J=8.8 Hz), 7.88 (2H, d, J=9.2 Hz)

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 3 hours
3. temperatureAfter cooling
4. concentrationthe mixture was concentrated to dryness
5. additionA chloroform-methanol mixed solution (1:1 (v/v)) was added to the residue
6. filtrationfiltered with Celite
7. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-d8761762b9aa4c20906f285c5a532ec3

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06069149