Sodium Hydroxide → Methyl hydrogen 2-nitroterephthalate

HRID 965274Notes

Reaction equation

HRID 965274 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-:3])=[O:2].[OH-].[Na+]>O1CCOCC1.O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21364Dimethyl nitroterephthalate

Product 1

HCID 98592Methyl hydrogen 2-nitroterephthalateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of di-methyl nitroterephthalate ((5), 12g, 50 mMol) in dioxane (100 mL) at room temperature was slowly added dropwise aq. 1N NaOH (50 mL) over 30 minutes. After stirring for 16 h at room temperature the reaction was diluted with water, washed with ether, acidified with aq. 1N HCl (50 mL) then extracted with 10% n-BuOH in ethyl acetate (2×100 mL). After drying (MgSO4) over ethyl acetate and evaporation under reduced pressure the resulting residue was purified by flash chromatography on silica gel eluted with (98:2:0.1) CHCl3, MeOH, HOAc to give product (6) (8.07 g, 72%) as a white solid.

Workup

  1. washwashed with ether
  2. extractionthen extracted with 10% n-BuOH in ethyl acetate (2×100 mL)
  3. dry with materialAfter drying (MgSO4)
  4. customover ethyl acetate and evaporation under reduced pressure the resulting residue
  5. customwas purified by flash chromatography on silica gel
  6. washeluted with (98:2:0.1) CHCl3, MeOH, HOAc

Sources & evidence

ORD record
ord-3bf20528fd3a46a7a337d991f2039c57
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

Loading…