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

HRID 1096588Notes

Reaction equation

HRID 1096588 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. 1H NMR (δ, 250 MHz, DMSO-d6): 1.32 (d, 6-H, CH3), 4.88 (septet, 1-H, CH), 7.37 (d, 1-H, aromatic), 8.32 (dd, 1-H, aromatic), 8.40 (d, 1-H, aromatic), 13.13 (s, 1-H, CO2H). 2-Isopropoxy-5-nitrobenzoic acid (6.02 g, 26.75 mmol) was suspended in EtOH (100 ml) and 10% Pd on C (wet basis) (600 mg) was added. The mixture was hydrogenated at 50 psi for 2 hrs. The mixture was filtered through celite and the volatiles were removed in vacuo. The residue was triturated with IPA, and the resulting solid filtered off, washed with MTBE and dried in vacuo to give 4.15 g of 5-amino-2-isopropoxybenzoic acid (79.5%) as a pale 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-46864b1840044770a8f4c730e924b18d
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

Loading…