Phosphorus oxychloride → Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl ester

HRID 251816Notes

Reaction equation

HRID 251816 reaction equation
O=P(Cl)(Cl)Cl.[C:6]([C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=O)[NH2:7]>ClCCCl>[C:6]([C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])#[N:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57686816HCID 57686816, compound

Product 1

HCID 21942473Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl esterYield 90.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

POCl3 (20 mmol) was added to the solution of methyl 3-carbamoyl-5-(2-methoxyethoxy)benzoate (15 mmol) in 35 ml 1,2-dichloroethane and stirred for 5 h at reflux. Then the solution was cooled to room temperature, poured to the ice-water and extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated to yield methyl 3-cyano-5-(2-methoxyethoxy)benzoate (90.5%).

Workup

  1. temperatureat reflux
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2fbeac0205e94b04858c3644e0163e50
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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