Lithium Hydroxide → 3-Nitro-4-propoxybenzoic acid

HRID 717719Notes

Reaction equation

HRID 717719 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1COCCC)[C:7]([O-:9])=[O:8])([O-:3])=[O:2].[Li+].[OH-].[CH2:20]1C[O:23][CH2:22][CH2:21]1>CCO.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:23][CH2:22][CH2:21][CH3:20])[C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 666150553-Nitro-4-propoxymethylbenzoate

Product 1

HCID 215462473-Nitro-4-propoxybenzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-nitro-4-propoxymethylbenzoate (0.35 g, 1.46 mmol) in a mixture of THF and EtOH (3 ml:1 ml) the solution of LiOH (0.345 g; 15 mmol) in H2O (1 ml) was added and the mixture was stirred for 4 h at room temperature. The solvent was distilled off and the residue was treated with 1 M HCl and extracted with EtOAc (50 ml). The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.32 g, 97%), as creamy solid. 1H NMR (CDCl3) 8.53 (d, 1H, J=1.65 Hz); 8.21 (dd, 1H, J=8.79, 1.62 Hz); 7.12 (d, 1H, J=8.82 Hz); 4.14 (t, 2H, J=6.39 Hz); 1.94-1.82 (m, 2H); 1.07 (t, 3H, J=7.35 Hz).

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. additionthe residue was treated with 1 M HCl
  4. extractionextracted with EtOAc (50 ml)
  5. washThe organic layer was washed with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-07fc751663df42c386c257eea217f55b
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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