Boron trifluoride → HCID 86741070, compound

HRID 2290595Notes

Reaction equation

HRID 2290595 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19].B(F)(F)F>F>[C:18]([OH:20])(=[O:19])[CH3:17].[C:18]([OH:20])(=[O:19])[CH3:17].[OH:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)=[CH:6][CH:5]=1)=[O:19]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 71034-HydroxybiphenylHCID 74203-Hydroxybenzoic Acid

Product 1

HCID 86741070HCID 86741070, compound

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent

Conditions

Temperature
25 °C

Procedure

One hundred seventy grams (1 mole) of p-phenylphenol, 138 grams (1 mole) of 3-hydroxybenzoic acid, 400 mL of hydrogen fluoride (HF), and 170 grams of boron trifluoride were reacted for 15 hours at 0° C. under autogenous pressure in an autoclave. Then the contents were mixed in excess water/ice to precipitate a green solid. After filtering and washing with water to remove the remaining HF, the powder was slurried with water, neutralized with 80 grams sodium bicarbonate (NaHCO3) until pH=8, filtered, and washed with water. After drying at 25° C. in air for 10 hours, the solid was dissolved in 3000 ml ethyl acetate, stirred overnight, and precipitated in a blender with 6000 ml n-hexane by volume. The solid was separated by filtration, washed two times with n-hexane, and dried at 120° C. under vacuum. The product was 160 grams of a beige crystalline solid which was determined by NMR analysis to be the 3-hydroxy,4'(4 -hydroxyphenyl)-benzophenone. This solid was acetylated directly by refluxing 3 hours with 640 ml of acetic anhydride and one drop of concentrated sulfuric acid. The solution was cooled to 25° C. and allowed to stand overnight. The solid was filtered, washed with methanol, and dried at 90° C. under vacuum. The product was 150 grams of 100% pure 3-hydroxy, 4'-(4-hydroxyphenyl)benzophenone diacetate as determined by NMR analysis. Its melting point was 120°-121° C.

Workup

  1. customto precipitate a green solid
  2. filtrationAfter filtering
  3. washwashing with water
  4. customto remove the remaining HF
  5. filtrationfiltered
  6. washwashed with water
  7. customAfter drying at 25° C. in air for 10 hours
  8. dissolutionthe solid was dissolved in 3000 ml ethyl acetate
  9. customprecipitated in a blender with 6000 ml n-hexane by volume
  10. customThe solid was separated by filtration
  11. washwashed two times with n-hexane
  12. customdried at 120° C. under vacuum
  13. temperatureby refluxing 3 hours with 640 ml of acetic anhydride and one drop of concentrated sulfuric acid
  14. waitto stand overnight
  15. filtrationThe solid was filtered
  16. washwashed with methanol
  17. customdried at 90° C. under vacuum

Sources & evidence

ORD record
ord-da4983da52ee4f279a83c5faa4545f51
Source dataset
uspto-grants-1986_10
Patent number
US04617369

Reaction notes

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