Methanol → Quizalofop

HRID 1534310Notes

Reaction equation

HRID 1534310 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][C:15]1[CH:27]=[CH:26][C:18]([O:19][CH:20]([CH3:25])[C:21]([O:23]C)=[O:22])=[CH:17][CH:16]=1)[CH:8]=[N:7]2.[OH-].[Na+]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]([CH3:25])[C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1)[CH:8]=[N:7]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 187101Quizalofop-methyl

Product 1

HCID 178795QuizalofopYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a mixture of methanol (10 ml) and tetrahydrofuran (14 ml), methyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionate (0.6 g) was dissolved, and lN sodium hydroxide solution (2.5 ml) was added thereto. The reaction was carried out at room temperature while stirring for 2 hours. After removal of methanol and tetrahydrofuran by distillation, the aqueous layer was washed with dichloromethane (1 ml), made acidic with conc. hydrochloric acid and extracted with ethyl acetate. The extract was concentrated to remove ethyl acetate to give 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionic acid (0.44 g). Yield, 76%.

Workup

  1. dissolutionwas dissolved
  2. customwas carried out at room temperature
  3. customAfter removal of methanol and tetrahydrofuran
  4. distillationby distillation
  5. washthe aqueous layer was washed with dichloromethane (1 ml)
  6. extractionextracted with ethyl acetate
  7. concentrationThe extract was concentrated
  8. customto remove ethyl acetate

Sources & evidence

ORD record
ord-f86923cfcf2f4d39857ee1f34d5789d9
Source dataset
uspto-grants-1992_02
Patent number
US05089043

Reaction notes

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