Benzoic Acid → 2,4-Dihydroxybenzophenone

HRID 493195Notes

Reaction equation

HRID 493195 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](O)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(F)(F)F>CC([O-])=O.[Na+]>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 5054ResorcinolHCID 6356Boron trifluoride

Product 1

HCID 85722,4-DihydroxybenzophenoneYield 46.4%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Procedure

Resorcinol (1.10 g, 10.0 mmol) and benzoic acid (1.22 g, 1.01 eq.) were treated with BF3-etherate (7.55 mL, 6 eq.) and heated for 2 h to 95° C. After cooling the reaction mixture was carefully poured onto 500 mL of 10% aq. NaOAc solution, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, heptane/AcOEt=8/2), followed by direct crystallization after reducing the volume, afforded 0.994 g of the title compound as off-white crystals.

Workup

  1. temperatureheated for 2 h to 95° C
  2. temperatureAfter cooling the reaction mixture
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customFlash chromatography (SiO2, heptane/AcOEt=8/2), followed by direct crystallization

Sources & evidence

ORD record
ord-9c705e1c3d724b0fac5b7294b1f2afb5
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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