Lithium Hydroxide → 3-Nitro-4-propoxybenzoic acid

HRID 2046124Notes

Reaction equation

HRID 2046124 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 1M 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 1M 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-43afa9337e4949d7a386330b88f75426
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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