4-Chlorophenol → Methyl 4-(p-chlorophenoxy)butyrate

A mixture of methyl 4-bromobutyrate (1.5 g, 8.29 mmol), 4-chlorophenol (1.17 g, 9.11 mmol), potassium carbonate (2.86 g, 20.7 mmol), and anhydrous N,N-dimethylformamide (5 mL) was added to a 25 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at room temperature for 16 hours. Progress of the reaction was monitored by analytical HPLC with UV detection (Rt=6.5 min). The mixture was added to stirring ice/water (150 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient elution of 0-100% ethyl acetate in hexanes to afford the title compound as a clear oil (1.45 g, 76% yield).

1. additionwas added to a 25 mL RBF with a magnetic stirring bar
2. additionThe mixture was added
3. extractionextracted with ethyl acetate (2×30 mL)
4. washThe combined organic layers were washed with saturated aqueous NaCl (2×30 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by silica gel column chromatography
9. washa gradient elution of 0-100% ethyl acetate in hexanes

ORD record

ord-1780b87f65d04fc69c623c72904937e6

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163027B2