Phenol → HCID 86741071, compound

HRID 2290596Notes

Reaction equation

HRID 2290596 reaction equation
C1(O)C=CC=CC=1.OC1C=[C:11](C=CC=1)[C:12]([OH:14])=[O:13].F.B(F)(F)F.[OH:23][C:24]1[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=1)[C:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:28]>S(=O)(=O)(O)O.C(OC(=O)C)(=O)C>[C:12]([OH:14])(=[O:13])[CH3:11].[C:12]([OH:14])(=[O:13])[CH3:11].[OH:23][C:24]1[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=1)[C:27]([C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1)=[O:28]

Participants

8

Reactant 5

HCID 996PhenolHCID 6356Boron trifluorideHCID 74203-Hydroxybenzoic AcidHCID 14917Hydrofluoric AcidHCID 110851543,4'-dihydroxybenzophenone

Product 1

HCID 86741071HCID 86741071, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Ninety-four grams (1 mole) of phenol, 138 grams (1 mole) of 3-hydroxybenzoic acid, 400 ml of hydrogen fluoride (HF), and 170 grams of boron trifluoride were allowed to react for 15 hours at 0° C. under autogeneous pressure in an autoclave. Then the reactor contents were mixed in excess water/ice. After filtering and washing the resulting green solid with water to remove the remaining HF, the powder was slurried with water, neutralized with sodium bicarbonate (NaHCO3) solution until pH=8, filtered and finally washed with water. After drying at 25° C. in air for 10 hours and under vacuum at 120° C. for 12 hours, there was obtained 160 grams of a beige, crystalline solid which was determined by NMR analysis to be 3,4'-dihydroxybenzophenone. The solid was acetylated directly by refluxing 3 hours with 640 ml of acetic anhydride and one drop of concentrated sulfuric acid. The solution was added to ice/water. The resultant solid was filtered, washed with cold methanol, and dried at 60° C. under vacuum. There was obtained 150 grams of pure 3,4'-dihydroxybenzophenone diacetate as determined by NMR analysis. Its melting point was 83°-84° C.

Workup

  1. customto react for 15 hours at 0° C. under autogeneous pressure in an autoclave
  2. filtrationAfter filtering
  3. washwashing the resulting green solid with water
  4. customto remove the remaining HF
  5. filtrationfiltered
  6. washfinally washed with water
  7. customAfter drying at 25° C. in air for 10 hours and under vacuum at 120° C. for 12 hours
  8. customthere was obtained 160 grams of a beige, crystalline solid which
  9. filtrationThe resultant solid was filtered
  10. washwashed with cold methanol
  11. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-eb854079910e48b58b030c388bd5ef4c
Source dataset
uspto-grants-1986_10
Patent number
US04617369

Reaction notes

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