Trifluoroacetic anhydride → Isoxepac

HRID 894187Notes

Reaction equation

HRID 894187 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)([OH:3])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[O:3]=[C:1]1[C:4]2[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=2[CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]1=2

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 122923092-((4-Carboxymethylphenoxy)methyl)benzoic acid

Product 1

HCID 41448Isoxepac

Procedure

Suspend 12 gm. of the carboxybenzyloxyphenylacetic acid of Step A in 50 ml. of trifluoroacetic anhydride in a pressure bottle and stir at 70° to 80° C. for 2.25 hours. Evaporate the reaction mixture to a syrup. Dissolve in 50 ml. of tetrahydrofuran and treat with sodium carbonate until pH 8. Stir for 15 minutes and acidify with 5 N HCl. Dilute with water and extract with ether. Wash the extract with water and dry over magnesium sulfate. Concentrate to dryness and recrystallize from ethyl acetate/hexane to obtain the title product.

Workup

  1. customEvaporate the reaction mixture to a syrup
  2. dissolutionDissolve in 50 ml
  3. additionof tetrahydrofuran and treat with sodium carbonate until pH 8
  4. additionDilute with water
  5. extractionextract with ether
  6. washWash the
  7. extractionextract with water
  8. dry with materialdry over magnesium sulfate
  9. concentrationConcentrate to dryness
  10. customrecrystallize from ethyl acetate/hexane

Sources & evidence

ORD record
ord-09dc4a5b8f944c2b8cf1bc7c6a5356d5
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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