Hydrochloric Acid → 5-Cyano-2-methoxybenzoic acid

HRID 1028187Notes

Reaction equation

HRID 1028187 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>O1CCCC1.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 Example 25A (6.1 g, 31.9 mmol) and lithium hydroxide monohydrate (5.36 g, 128 mmol) in tetrahydrofuran (100 mL) and H2O (50 mL) was stirred at room temperature for 3 h. The reaction pH was adjusted to pH=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, CHLOROFORM-D) 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-eef427b2ad1f481a9a1033bb8c4670d6
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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