Hydrochloric Acid → 2-(1-Methylethoxy)-5-nitrobenzoic acid

HRID 2098398Notes

Reaction equation

HRID 2098398 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.O>[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66781497HCID 66781497, compound

Product 1

HCID 44473202-(1-Methylethoxy)-5-nitrobenzoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-isopropoxy-5-nitrobenzoate (6.92 g, 28.95 mmol) was taken up in THF/H2O (35 ml of each) and LiOH (1.39 g, 57.9 mmol) was added. The mixture was stirred at RT overnight then the pH was lowered to 1 by the addition of concentrated HCl and the product extracted in ethyl acetate (50 ml). The organic layer was dried (MgSO4) and evaporated to give 2-isopropoxy-5-nitrobenzoic acid (6.02 g, 92.5%) as a yellow solid.

Workup

  1. additionwas added
  2. extractionthe product extracted in ethyl acetate (50 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-94a26213bd9c446393ac8f8eeed34464
Source dataset
uspto-grants-2013_05
Patent number
US08450506B2

Reaction notes

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