Hydrochloric Acid → 5-Cyano-2-methoxybenzoic acid

HRID 253616Notes

Reaction equation

HRID 253616 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, 3H) 7.17 (d, J=8.85 Hz, 1H) 7.86 (dd, J=8.85, 2.44 Hz, 1H) 8.47 (d, J=2.14 Hz, 1H).

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-b0d69f7fc07c411fb15f2a9e2c5fd2ff
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Reaction notes

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