Lithium Hydroxide → 5-(2-Benzyloxy-ethoxy)-2-nitro-benzoic acid

HRID 1955249Notes

Reaction equation

HRID 1955249 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:22]([O-:24])=[O:23])=[C:16]([CH:21]=1)[C:17]([O:19]C)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:22]([O-:24])=[O:23])=[C:16]([CH:21]=1)[C:17]([OH:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23294552Methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoate

Product 1

HCID 127191835-(2-Benzyloxy-ethoxy)-2-nitro-benzoic acidYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoate (8.26 g, 24.93 mmol) in methanol (200 ml) was added LiOH (1N, 80 ml), and the reaction mixture was heated to 50° C. for 2 h. The solvent was evaporated, water was added (100 ml), and the solution was cooled in an ice bath. 3N HCl was added slowly to pH=2.5. The aqueous layer was salted with NaCl and extracted with ethyl acetate (4×75 ml). The aqueous layer was reacidified and extracted with ethyl acetate (100 ml). The combined organic extracts were washed with brine (100 ml), dried over MgSO4, filtered and evaporated to give an oil that solidified upon standing. The solid was washed with ether (30 ml), filtered and air dried to give 5-(2-benzyloxy-ethoxy)-2-nitro-benzoic acid (5.99 g, 75%). 1H NMR (CDCl3) 7.96 (1H, d, J=9.0), 7.36-7.25 (5H, m), 7.17 (1H, d, J=2.7), 7.05 (1H, dd, J=9.0, 2.7), 4.62 (2H, s), 4.22 (2H, m), 3.84 (2H, m).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added (100 ml)
  3. temperaturethe solution was cooled in an ice bath
  4. addition3N HCl was added slowly to pH=2.5
  5. extractionextracted with ethyl acetate (4×75 ml)
  6. extractionextracted with ethyl acetate (100 ml)
  7. washThe combined organic extracts were washed with brine (100 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give an oil that
  12. washThe solid was washed with ether (30 ml)
  13. filtrationfiltered
  14. customair dried

Sources & evidence

ORD record
ord-8581da87875e4336bf5ab791b4c4774c
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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