Hydrochloric Acid → Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

Ethyl 4,5-dimethoxy-2-nitrobenzoate (10.22 g, 40.04 mmol) was refluxed in 20% aqueous NaOH (50 mL) for 2 days. The solution was cooled, acidifed to pH 2 using concentrated HCl, and the resulting solid filtered, washed with water and dried. The solid was dissolved in methanol (90 mL) and thionyl chloride (3.1 mL, 42.75 mmol) cautiously added. After refluxing for 3 days, the solution was cooled, concentrated and diluted with dichloromethane (280 mL). The organic phase was washed with water (200 mL) and the aqueous layer further extracted with dichlormethane (100 mL). Organic layers were combined, dried (MgSO4) and concentrated to give the title compound as a yellow solid (6.00 g, 66%).

1. temperatureThe solution was cooled
2. filtrationthe resulting solid filtered
3. washwashed with water
4. customdried
5. dissolutionThe solid was dissolved in methanol (90 mL)
6. temperatureAfter refluxing for 3 days
7. temperaturethe solution was cooled
8. concentrationconcentrated
9. additiondiluted with dichloromethane (280 mL)
10. washThe organic phase was washed with water (200 mL)
11. extractionthe aqueous layer further extracted with dichlormethane (100 mL)
12. dry with materialdried (MgSO4)
13. concentrationconcentrated

ORD record

ord-ff14fe30aabc4b55a18f9be5cb7f110a

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324226B2