3-Benzoylbenzoic acid → 3-(Hydroxymethyl)benzophenone

HRID 2307657Notes

Reaction equation

HRID 2307657 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.C(OCC)C>[OH:13][CH2:12][C:11]1[CH:10]=[C:9]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 1013863-Benzoylbenzoic acid

Product 1

HCID 127837393-(Hydroxymethyl)benzophenone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-benzoylbenzoic acid (6.26 g, 27.7 mmol) was carefully added in several portions to borane-N,N-diethylaniline complex (7.38 mL, 41.5 mmol) in anhydrous THF (60 mL) at ambient temperature. After 15 minutes, the reaction mixture was heated at reflux for 5 hours and then cooled to ambient temperature. The reaction mixture was diluted with diethyl ether, quenched with 1N HCl and the separated aqueous phase was extracted with diethyl ether. The organic layers were combined, washed with 1N HCl, brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 40% ethyl acetate/hexanes) to provide a mixture of the title compound and the diol, [3-(hydroxymethyl)phenyl](phenyl)methanol, as a colorless oil (3.59 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. customquenched with 1N HCl
  4. extractionthe separated aqueous phase was extracted with diethyl ether
  5. washwashed with 1N HCl, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, 40% ethyl acetate/hexanes)
  10. customto provide

Sources & evidence

ORD record
ord-6b19a89c6093494bb89687cc62019485
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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