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

HRID 1773397Notes

Reaction equation

HRID 1773397 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ecaa6e535ab4e829831aae6785c0a7f
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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