反应详情

温度

180 °C

A mixture of ethyl 5-iodo-2-methoxybenzoate (4.1 g, 13.4 mmol), sodium phenoxide (1.7-1.8 g, 15 mmol), copper(I) oxide (1.1 g, 7.5 mmol) and dimethylacetamide (approximately 15 mL) was heated 4 hours with stirring at 180° C. The mixture was filtered, diluted with water and extracted with pentane/diethyl ether (7:3, 2× 100 mL). The combined extracts were washed with dilute sodium hydroxide (3×) and water (1×), dried (K2CO3), filtered and concentrated. The residue was dried (P2O5) under vacuum to give crude product (1.17 g) which was combined with crude product (2.4 g) similarly prepared from methyl 5-iodo-2-methoxybenzoate (6 g, 19.6 mmol). The combined crude product was purified by column chromatography eluting with hexane/acetone (96:4) to give ethyl 2-methoxy-5-phenoxybenzoate (2 g, 7.3 mmol), m.p. 52°-52° C.

1. temperaturewas heated 4 hours
2. filtrationThe mixture was filtered
3. additiondiluted with water
4. extractionextracted with pentane/diethyl ether (7:3, 2× 100 mL)
5. washThe combined extracts were washed with dilute sodium hydroxide (3×) and water (1×)
6. dry with materialdried (K2CO3)
7. filtrationfiltered
8. concentrationconcentrated
9. dry with materialThe residue was dried (P2O5) under vacuum
10. customto give crude product (1.17 g) which
11. customwas purified by column chromatography
12. washeluting with hexane/acetone (96:4)