Acetic Acid → Acifluorfen

HRID 2296409Notes

Reaction equation

HRID 2296409 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9].C(OC(=O)C)(=O)C.C(O)(=O)C.OS(O)(=O)=O.[N+:38]([O-])([OH:40])=[O:39]>>[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:11]([N+:38]([O-:40])=[O:39])=[C:7]([CH:6]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Product 1

HCID 44073AcifluorfenYield 80.3%

Procedure

3-(2-Chloro-4-trifluoromethylphenoxy)benzoic acid (275.9 g, 0.935 mole), acetic anhydride (276 g, 2.7 mole), glacial acetic acid (276 g, 4.6 mole) and conc. H2SO4 (44 g) were charged into a three-neck 5 liter flask equipped with a mechanical stirrer, thermometer and an addition funnel. Nitric acid (90%, 91.7 g, 1.3 mole) was added at 15°-25° C. over 0.5 hr. The cooling bath was substituted with a water bath and the reaction was stirred for 1.5 hrs. at 30° C. The reaction was quenched with 1250 ml of water (at 30° C.), stirred for 0.25 hr. The resultant yellow precipitate was filtered and washed with 2 liters of water. Recrystallization from toluene (750 ml) afforded 271.6 g of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid; m.p. 120°-121° C.

Workup

  1. customequipped with a mechanical stirrer
  2. customThe cooling bath was substituted with a water bath
  3. customat 30° C
  4. customThe reaction was quenched with 1250 ml of water (at 30° C.)
  5. stirringstirred for 0.25 hr
  6. filtrationThe resultant yellow precipitate was filtered
  7. washwashed with 2 liters of water
  8. customRecrystallization from toluene (750 ml)

Sources & evidence

ORD record
ord-7f1a04a9a0554796bd977df73dd0ad29
Source dataset
uspto-grants-1984_01
Patent number
US04429146

Reaction notes

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