Hydrochloric Acid → 5-Cyano-2-methoxybenzoic acid

HRID 76254Notes

Reaction equation

HRID 76254 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].O.[OH-].[Li+].Cl>C1COCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 18464789Methyl 5-cyano-2-methoxybenzoate

Product 1

HCID 219425685-Cyano-2-methoxybenzoic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Example 26A (6.1 g, 31.9 mmol) and lithium hydroxide monohydrate (5.36 g, 128 mmol) in THF (100 mL) and H2O (50 mL) was stirred at rt for 3 hrs. The reaction pH was adjusted to 3 with 3N HCl, and the mixture was extracted twice with isopropanol/CH2Cl2 (1:3). The organics were combined, dried (MgSO4), filtered and concentrated to afford 5.6 g (99%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 4.15 (s, 3 H) 7.17 (d, J=8.85 Hz, 1 H) 7.86 (dd, J=8.85, 2.44 Hz, 1 H) 8.47 (d, J=2.14 Hz, 1 H).

Workup

  1. extractionthe mixture was extracted twice with isopropanol/CH2Cl2 (1:3)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2175cf89920a4fb1a4363bf961ce3332
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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