Methyl iodide → Methyl 5-cyano-2-methoxybenzoate

HRID 1946244Notes

Reaction equation

HRID 1946244 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[O:12][CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoateYield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of methyl-2-hydroxy-5-cyano-benzoate (2.g, 5.6 mmol), K2CO3 (4.68 g, 16.8 mmol) in acetone (50 ml) was added methyl iodide (0.7 ml, 5.6 mmol). The reaction was then heated at 65° C. overnight resulting in formation of a solid which was filtered off whilst hot and washed with acetone to give 5-cyano-2-methoxy-benzoic acid methyl ester (0.45 g). The crude product was dissolved in THF (5 ml) and then treated with LiOH (0.108 g 0.26 mmol) in water (5 ml) and stirred at room temperature overnight. The reaction was acidified with 2M HCl and extracted EtOAc (×2). The organic portion dried (MgSO4) and reduced in vacuo to give 5-cyano-2-methoxy-benzoic acid (0.277 g). (LC/MS Acidic: Rt 2.92, [M+H]+ 178).

Workup

  1. customresulting in formation of a solid which
  2. filtrationwas filtered off whilst hot and
  3. washwashed with acetone

Sources & evidence

ORD record
ord-f323b2eee341435da7b314b34bd11ded
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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