Boron trifluoride → 2-Benzoylbenzoic Acid

HRID 1701814Notes

Reaction equation

HRID 1701814 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.B(F)(F)F>C1C=CC=CC=1>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])(=[O:5])[C:2]1[CH:3]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6356Boron trifluorideHCID 6811Phthalic Anhydride

Product 1

HCID 68132-Benzoylbenzoic AcidYield 177%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

7.4 g of phthalic anhydride and 3.9 of benzene were charged at ambient temperature into a stainless steel autoclave. The autoclave was cooled by liquid nitrogen and 10 g of HF and 37.4 g of BF3 were introduced. The autoclave was heated to 20° C. and the pressure raised to 47 bars. The temperature was maintained at 20° C. for 15 minutes and the product degassed under reduced pressure in order to recover the catalyst. After washing with cold water, 10 g of crude o-benzoyl benzoic acid were obtained titrating 74.4% and containing 0.5% of anthraquinone, thus a chemical yield of 66%. After purification by extraction with 600 cm3 of boiling water, then crystallization by cooling to 20° C., o-benzoyl benzoic acid titrating 98.4% was obtained.

Workup

  1. additionwere introduced
  2. temperaturethe pressure raised to 47 bars
  3. temperatureThe temperature was maintained at 20° C. for 15 minutes
  4. customthe product degassed under reduced pressure in order
  5. customto recover the catalyst
  6. washAfter washing with cold water

Sources & evidence

ORD record
ord-9cc0ab097477443f810fc5244b17d3df
Source dataset
uspto-grants-1983_04
Patent number
US04379092

Reaction notes

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