Acetic Acid → HCID 14209253, compound

HRID 1252579Notes

Reaction equation

HRID 1252579 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[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(O)(=O)C.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[N+:41]([O-])([OH:43])=[O:42]>>[N+:41]([C:11]1[CH:12]=[CH:13][C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([C:18]([F:23])([F:24])[C:19]([F:22])([F:21])[F:20])=[CH:17][C:2]=2[Cl:1])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9])([O-:43])=[O:42]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 7918Acetic AnhydrideHCID 14209252HCID 14209252, compound

Product 1

HCID 14209253HCID 14209253, compoundYield 83.9%

Procedure

A 50 ml 3-neck round bottom flash was charged with 2.5 gm (6.83 mmol) of 3-(2-chloro-4-pentafluoroethylphenoxy)benzoic acid, 2.18 gm (2.08 ml, 36.19 mmol) of glacial acetic acid, 2.1 gm (20.49 mmol) of acetic anhydride and 70 mg (683 mmol) of concentrated sulfuric acid. The resulting slurry was stirred vigorously while cooling to 0°-5° C. with the aid of an icewater bath. To the cooled slurry was added dropwise a mixture 280 mg (2.73 mmol) of concentrated sulfuric acid and 620 mg (9.56 mmol) to 97% nitric acid (red fuming). The yellow solution was maintained at 0°-5° C. for about 1.5 hours at which time the reaction mixture was poured into stirred ice water. The gummy residue that formed in the bottom of the flask was extracted with 100 ml of ether, the ether layer separated, and the aqueous acid layer reextracted with a second portion of ether. The combined ether layers were washed with brine, dried and evaporated in vacuo leaving a yellow oil. Much of the yellow color was removed by dissolving the oil in 300 ml of chloroform and eluting through a pad of silica gel. Evaporation of the eluent yielded 2.36 gm (83.9%) of a light yellow oil which crystallized on standing. The product had the following elemental analysis, calculated (found): C: 43.76 (44.43); H: 1.71 (2.24); Cl: 8.61 (8.83); F: 23.07 (18.90); N: 3.40 (2.47); O: 19.43.

Workup

  1. temperaturewhile cooling to 0°-5° C. with the aid of an icewater bath
  2. temperatureThe yellow solution was maintained at 0°-5° C. for about 1.5 hours at which time the reaction mixture
  3. additionwas poured
  4. customThe gummy residue that formed in the bottom of the flask
  5. extractionwas extracted with 100 ml of ether
  6. customthe ether layer separated
  7. washThe combined ether layers were washed with brine
  8. customdried
  9. customevaporated in vacuo
  10. customleaving a yellow oil
  11. customMuch of the yellow color was removed
  12. dissolutionby dissolving the oil in 300 ml of chloroform
  13. washeluting through a pad of silica gel
  14. customEvaporation of the eluent

Sources & evidence

ORD record
ord-29fef08136c64ce8bfd4bfbbac08cd08
Source dataset
uspto-grants-1988_05
Patent number
US04743703

Reaction notes

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