Hydrochloric Acid → Methyl 2-(3-nitrophenoxy)phenylacetate

温度

130 °C

A mixture of 2-bromophenylacetic acid (21.5 g), 3-nitrophenol (29.2 g), potassium carbonate (27.6 g) and cuprous chloride (0.5 g) was heated with stirring at 130° C. for 6 hours. After cooling, the mixture was poured into water (500 ml), acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×200 ml). The extracts were dried, filtered and concentrated to give a dark oil. The oil was dissolved in methanol (400 ml) containing concentrated sulphuric acid (4 ml) and the resulting solution was heated at reflux for 3 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate (300 ml). This solution was washed successively with sodium hydroxide (2×100 ml of 1M aqueous solution) and brine, then dried, filtered and concentrated to give a dark oil. Bulb-to-bulb distillation of this oil (220° C. oven temperature, 0.2 mmHg) gave methyl 2-(3-nitrophenoxy)phenylacetate (16.74 g, 58% yield from 2-bromophenylacetic acid) as a clear pale oil.

1. temperaturewas heated
2. temperatureAfter cooling
3. extractionextracted with ethyl acetate (3×200 ml)
4. customThe extracts were dried
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a dark oil
8. temperaturethe resulting solution was heated
9. temperatureat reflux for 3 hours
10. concentrationThe reaction mixture was concentrated
11. dissolutionthe residue was dissolved in ethyl acetate (300 ml)
12. washThis solution was washed successively with sodium hydroxide (2×100 ml of 1M aqueous solution) and brine
13. customdried
14. filtrationfiltered
15. concentrationconcentrated
16. customto give a dark oil
17. distillationBulb-to-bulb distillation of this oil (220° C. oven temperature, 0.2 mmHg)

ORDレコード

ord-492f7075f4854e85958c5233f8ff6337

出典データセット

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05468857