反应详情

Bromocatecholborane (4.11 g, 20.7 mmol) is added to a solution of 1,6-dimethoxynaphthalene (3.89 g, 20.7 mmol) in dichloroethane (60 mL). The resulting solution is heated to reflux for 72 hours, allowed to cool, and then poured into 1N HCl. The resulting mixture is extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The product is purified by three columns (step gradient of 50–60–65%CH2Cl2 in hexanes) to give 5-methoxy-2-hydroxy naphthalene as an oil that solidifies on sitting (955 mg, 27%). 1H NMR (300 MHz, CDCl3) δ 8.17, 7.2–7.4, 7.0–7.1, 6.66, 5.08, 3.97.

1. temperatureThe resulting solution is heated
2. temperatureto reflux for 72 hours
3. temperatureto cool
4. extractionThe resulting mixture is extracted three times with CH2Cl2
5. dry with materialThe combined organic layers are dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. customThe product is purified by three columns (step gradient of 50–60–65%CH2Cl2 in hexanes)