Hydrochloric Acid → 4-(2-Chloroethoxy)-3-methoxybenzoic acid

Temperature

40 °C

In a 300 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 17.40 g (69.7 mmol) of methyl 4-(2-chloroethoxy)-3-methoxybenzoate, 69.7 mL of aqueous sodium hydroxide solution (2 mol/L), and 69.7 mL of methanol. The resulting mixture was heated to 40° C. for 4 hours in an argon gas atmosphere. After the reaction was complete, the reaction mixture was cooled to 10° C., and neutralized by 69.7 mL of hydrochloric acid (2 mol/L). The reaction mixture was then placed to distill methanol off, and cooled to 10° C., to precipitate a crystalline product. The crystalline product was collected and dried under reduced pressure, to give 15.5 g (isolated yield: 95.2%, purity: 99% in terms of area percentage by high performance liquid chromatography) of 4-(2-chloroethoxy)-3-methoxybenzoic acid as a white crystalline product.

1. customIn a 300 mL volume glass flask equipped with a stirrer
2. temperaturethe reaction mixture was cooled to 10° C.
3. distillationto distill methanol off, and
4. temperaturecooled to 10° C.
5. customto precipitate a crystalline product
6. customThe crystalline product was collected
7. customdried under reduced pressure

ORD record

ord-11e2d3978e81461bbf9af2c5c984e595

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367824B2