Propionate ion → Fluazifop-butyl

HRID 1648975Notes

Reaction equation

HRID 1648975 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:25]=[CH:24][C:13]([O:14][C:15](=[CH2:23])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[H][H].C([O-])(=O)CC>C(O)CCC.[Pd]>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]([CH3:23])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 104745Propionate ionHCID 20481507n-Butyl 2-[4-(5-trifluoromethylpyrid-2-yloxy)phenoxy]acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 50897Fluazifop-butyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Procedure

The product (15 g) from Step 3 in n-butanol (300 ml) was hydrogenated at room temperature and atmospheric pressure using a 10% palladium on carbon catalyst. When the uptake of hydrogen ceased, the catalyst was filtered off and the filtrate evaporated under reduced pressure. The residue was purified by short-path distillation (at 140°-150°/0.2 mmHg) to afford a main fraction (11.6 g) containing 57% w/w of the desired propionate which was recrystallised from cold hexane to give n-butyl 2-[4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]propionate. The propionate may then be obtained substantially pure by recrystallisation from cold hexane.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. distillationThe residue was purified by short-path distillation (at 140°-150°/0.2 mmHg)
  5. customto afford a main fraction (11.6 g)
  6. customwas recrystallised from cold hexane

Sources & evidence

ORD record
ord-e4248a7e14cb4d4ca79cf0131ba920b0
Source dataset
uspto-grants-1983_11
Patent number
US04414391

Reaction notes

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