Hydrochloric Acid → 2-(2-Methylphenoxy)acetic acid

Temperature

80 °C

To a stirred solution of o-cresol (200 mg, 1.85 mmol) in MeCN (5 mL) was added ethyl bromoacetate (461 mg, 2.78 mmol) and K2CO3 (766 mg, 5.55 mmol). The mixture was stirred at 80° C. for 4 hours. The mixture was filtered and the filtrate concentrated. NaOH (150 mg, 3.70 mmol) and H2O/EtOH (1:1, 10 mL) was then added to the mixture and the mixture stirred at 50° C. for 4 hours. After cooling, the mixture was acidified by adding 1M HCl then extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated. The residue was used directly in the next step without further purification.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate concentrated
3. stirringthe mixture stirred at 50° C. for 4 hours
4. temperatureAfter cooling
5. extractionthen extracted with ethyl acetate (2×30 mL)
6. washThe combined organic extracts were washed with brine (30 mL)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated
9. customThe residue was used directly in the next step without further purification

ORD record

ord-2200bda1fb224f718b8410aa5d968053

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266836B2