Hydrochloric Acid → (2,6-Dichloro-4-methoxyphenyl)methanol

Temperature

100 °C

To a mixture of 1,3-dichloro-5-methoxybenzene (10.0 g), paraformaldehyde (2.21 g), and concentrated hydrochloric acid (100 mL) was added concentrated sulfuric acid (1.00 mL) at room temperature. After heating and refluxing at 100° C. for 8 hours, and leaving to be cooled to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue were added dioxane (56.0 mL) and a 1 M aqueous sodium hydroxide solution (113 mL), followed by heating and refluxing at 100° C. for 3 hours. The reaction solution was left to be cooled, and then water was added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain (2,6-dichloro-4-methoxyphenyl)methanol (4.67 g).

1. temperatureAfter heating
2. customleaving
3. temperatureto be cooled to room temperature
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. additionTo the residue were added dioxane (56.0 mL)
9. temperatureby heating
10. temperaturerefluxing at 100° C. for 3 hours
11. waitThe reaction solution was left
12. temperatureto be cooled
13. additionwater was added
14. extractionfollowed by extraction with chloroform
15. washThe organic layer was washed with a saturated aqueous sodium chloride solution
16. dry with materialdried over anhydrous magnesium sulfate
17. concentrationconcentrated under reduced pressure
18. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-a1c6494bf7404a0e8ee7f0762398b550

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199927B2