2-Chloropropionic acid → Fluazifop

HRID 1589719Notes

Reaction equation

HRID 1589719 reaction equation
Cl[CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[F:7][C:8]([F:24])([F:23])[C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:13][CH:14]=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1.O>[F:24][C:8]([F:7])([F:23])[C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH:2]([CH3:6])[C:3]([OH:5])=[O:4])=[CH:20][CH:21]=2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 117342-Chloropropionic acidHCID 14798Sodium HydroxideHCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenol

Product 1

HCID 91701Fluazifop

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

100.0 g (0.92 mol) of (RS)-(+)-2-chloropropionic acid are added to the solution of 192.0 g (0.75 mol) of 4-(5-trifluoromethyl-2-pyridyloxy)phenol in 900 g (about 1050 ml) of xylene. The temperature of the reaction mixture is elevated to 80° C. and 78.0 g (1.95 mol) of sodium hydroxide dissolved in water are added dropwise under such a reduced pressure (about 36 kPa) that the mixture boils at 90° C. The water formed in the reaction is continuously distilled off while maintaining the boiling temperature at 90° C. After the addition, the reaction mixture is stirred at 90° C. for additional 15 minutes, then the reduced pressure is ceased. After adding 300 ml of water to the mixture and stirring at 85° C. for 10 minutes, it is acidified by adding phosphoric acid and the phases are separated. The xylene layer is dried, treated with activated charcoal and finally evaporated to dryness.

Workup

  1. customis elevated to 80° C.
  2. distillationis continuously distilled off
  3. additionAfter the addition
  4. additionAfter adding 300 ml of water to the mixture
  5. stirringstirring at 85° C. for 10 minutes
  6. additionby adding phosphoric acid
  7. customthe phases are separated
  8. dry with materialThe xylene layer is dried
  9. additiontreated with activated charcoal
  10. customfinally evaporated to dryness

Sources & evidence

ORD record
ord-f1f8c5de65c94a25b60eff0ab9b5d3fc
Source dataset
uspto-grants-1993_04
Patent number
US05199970

Reaction notes

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