Thionyl Chloride → Methyl 5-cyano-2-methoxybenzoate

HRID 637204Notes

Reaction equation

HRID 637204 reaction equation
CO[C:3]1C=C[C:11]([CH:14]=[O:15])=[CH:10][C:4]=1[C:5](=[N:8]O)OC.S(Cl)(Cl)=O.[C:20]([O:23][CH2:24]C)(=[O:22])[CH3:21].[CH3:26]CCCCC>ClCCl>[CH3:26][O:15][C:14]1[CH:11]=[CH:10][C:4]([C:5]#[N:8])=[CH:3][C:21]=1[C:20]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 21226206Ethyl acetate hexaneHCID 86583897Methyl 2-methoxy-5-formylbenzoate oxime

Product 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine methyl 2-methoxy-5-formylbenzoate oxime (3.5 g, 16.7 mmol) in dichloromethane (75 mL) and cool in an ice-bath. Add dropwise thionyl chloride (2.0 mL, 27.2 mmol). After 20 minutes, dilute the reaction mixture with dichloromethane and extract with a saturated aqueous solution of sodium bicarbonate and then brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give methyl 2-methoxy-5-cyanobenzoate.

Workup

  1. extractionextract with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a residue

Sources & evidence

ORD record
ord-f605c7d41ba2402397b128c49938f2f8
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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