4-Nitrophenol → 1-[(2-methoxyethoxy)methoxy]-4-nitroBenzene

Temperature

0 °C

In a 50 mL, 3-neck RBF equipped with a magnetic stirrer, reflux condenser, calcium chloride guard tube and thermometer pocket were sequentially charged 4-nitrophenol (1.50 g), DIPEA (2.90 mL) and DCM (25 mL). MEM-Cl (2.016 g) was added drop wise to the reaction at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to stir at room temperature for 4 hours. The reaction was monitored on TLC using hexane:ethyl acetate (8:2) as mobile phase. After completion, the reaction was poured into water and the product was extracted in ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure to give 2.35 g of 1-[(2-methoxyethoxy)methoxy]-4-nitrobenzene as a solid, which was used in the next step without further purification.

1. customIn a 50 mL, 3-neck RBF equipped with a magnetic stirrer
2. temperaturereflux condenser, calcium chloride guard tube
3. customwise to the reaction at 0° C
4. stirringto stir at room temperature for 4 hours
5. extractionthe product was extracted in ethyl acetate
6. washwashed with brine
7. dry with materialThe organic layer was dried over sodium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-5c994c2bb51347598683b2fd763a399e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09415049B2