p-Toluenesulfonic acid monohydrate → Methyl 4-cyano-2-methoxybenzoate

HRID 909104Notes

Reaction equation

HRID 909104 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1)#[N:2].O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 151660044-Cyano-2-methoxybenzoic acid

Product 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoateYield 367.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-cyano-2-methoxybenzoic acid (1.00 g, 5.648 mmol, Biogene) in methanol (15.0 mL) was added p-toluenesulfonic acid monohydrate (286 mg, 1.48 mmol, Aldrich) and it was heated to reflux under an argon atmosphere for 16 hrs. The solvent was removed and the reaction mixture was extracted with EtOAc, washed with saturated Na2CO3, water, and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-cyano-2-methoxy-benzoic acid methyl ester (1.04 g, 96.4%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an argon atmosphere for 16 hrs
  3. customThe solvent was removed
  4. extractionthe reaction mixture was extracted with EtOAc
  5. washwashed with saturated Na2CO3, water, and saturated NaCl
  6. customThe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d3b7d81ef4b46ae93156d04e02dee91
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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