4-Chlorophenol → 2-(4-Chlorophenoxy)ethanol

Temperature

80 °C

A mixture of 4-chlorophenol (5.61 g, 43.65 mmol), 2-bromoethanol (6.0 g, 48.0 mmol), sodium hydroxide (2.62 g, 65.47 mmol), and water (18 mL) was added to a 50 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and warmed in an oil bath at 80° C. The solution was heated for 19 hours. Progress of the reaction was monitored by analytical HPLC with UV detection. The reaction mixture was partitioned using ethyl acetate (100 mL) and water (50 mL). The aqueous layer was extracted once more with ethyl acetate (40 mL). The combined organic layer was washed with 1N NaOH (6×40 mL) and saturated aqueous NaCl (40 mL), dried (Na2SO4), filtered, and concentrated. The crude mixture was purified by silica gel column chromatography using 30-100% ethyl acetate in hexanes to afford the title compound as a clear oil (5.67 g, 75% yield).

1. additionwas added to a 50 mL RBF with a magnetic stirring bar
2. customThe flask was fitted with a condenser
3. temperatureThe solution was heated for 19 hours
4. customThe reaction mixture was partitioned
5. extractionThe aqueous layer was extracted once more with ethyl acetate (40 mL)
6. washThe combined organic layer was washed with 1N NaOH (6×40 mL) and saturated aqueous NaCl (40 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude mixture was purified by silica gel column chromatography

ORD record

ord-f50b24eebc534c40bc772e75096a2be7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163027B2