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

HRID 1526031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526031
C[O:2][C:3](=[O:20])[C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:6]([N+:17]([O-:19])=[O:18])[CH:5]=1.O.[OH-].[Li+]>C1COCC1.O>[C:11]([O:10][C:8](=[O:9])[C:7]1[CH:15]=[CH:16][C:4]([C:3]([OH:20])=[O:2])=[CH:5][C:6]=1[N+:17]([O-:19])=[O:18])([CH3:14])([CH3:12])[CH3:13]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 675127822-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester

Produkt 1

HCID 686717752-Nitro-terephthalic acid 1-tert-butyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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) The aqueous phase
  6. additionwas 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

Quellen und Nachweise

ORD-Eintrag
ord-77c07ae75c874d7bae8703357784eea0
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085558B2

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