Phosphoric Acid → Trifop

HRID 1105666Notes

Reaction equation

HRID 1105666 reaction equation
Cl[CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].[F:9][C:10]([F:26])([F:25])[C:11]1[CH:24]=[CH:23][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1.P(=O)(O)(O)O>O.C1(C)C(C)=CC=CC=1>[F:9][C:10]([F:25])([F:26])[C:11]1[CH:24]=[CH:23][C:14]([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)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 117342-Chloropropionic acidHCID 14798Sodium HydroxideHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenol

Product 1

HCID 181206Trifop

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

132.5 Parts of 2-chloropropionic acid (98% strength) and 199 parts of 50% sodium hydroxide solution are added simultaneously but separately at 110°-115° C. to a solution of 254 parts of 4-(4'-trifluoromethylphenoxy)-phenol in 1,000 parts of xylene. During the addition, the reaction temperature is maintained by azeotropic distillation of water in a water trap. The addition being complete, stirring is continued for 15 minutes at 110°-115° C., the batch is cooled to 90° C. and after addition of 400 parts of water, it is stirred for a further 10 minutes at 85° C., then acidified at this temperature with 120 parts of phosphoric acid, and stirred for a further 10 minutes. After elimination of the water phase, xylene is distilled off in a water jet vacuum, and the solids are dried at 60° C. and 250 mbar. 326 parts of 2-[4'-(4" -trifluoromethylphenoxy)-phenoxy]-propionic acid are obtained. The content of pure final product is 99.6% corresponding to a yield of 99.6% of theory. The residual content of 4-(4'-trifluoromethyl-phenoxy)-phenol is 0.35%.

Workup

  1. additionDuring the addition
  2. additionThe addition
  3. stirringis stirred for a further 10 minutes at 85° C.
  4. stirringstirred for a further 10 minutes
  5. distillationAfter elimination of the water phase, xylene is distilled off in a water jet vacuum
  6. customthe solids are dried at 60° C.

Sources & evidence

ORD record
ord-56a3117fab404cd69be75e08df15c134
Source dataset
uspto-grants-1982_01
Patent number
US04309547

Reaction notes

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