Lithium hydroxide, monohydrate → 2-Nitro-terephthalic acid 1-tert-butyl ester

2-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester (21.49 mmol) was dissolved in THF (143 mL) and treated with lithium hydroxide monohydrate (1.35 g, 32.24 mmol) in water (97 mL). The reaction was stirred at room temperature for 2 hours then partially evaporated, cooled with an ice/water bath and treated with 1N HCl dropwise (35 mL). Precipitation of a solid occurred. The mixture was then extracted with DCM (150 mL and 2×50 mL). The aqueous phase was further treated with 1N HCl (10 mL) and extracted with DCM (2×50 mL). The combined organic layers were then washed with water and finally with brine. After drying over sodium sulphate and evaporation, 5.34 g of title compound were obtained as a reddish solid in 93% overall yield.

1. customthen partially evaporated
2. temperaturecooled with an ice/water bath
3. additiontreated with 1N HCl dropwise (35 mL)
4. customPrecipitation of a solid
5. extractionThe mixture was then extracted with DCM (150 mL and 2×50 mL)
6. additionThe aqueous phase was further treated with 1N HCl (10 mL)
7. extractionextracted with DCM (2×50 mL)
8. washThe combined organic layers were then washed with water and finally with brine
9. dry with materialAfter drying over sodium sulphate and evaporation

ORD-Eintrag

ord-e8def1532f0a43f58fa7a400e83b2a2e

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08673893B2