Acetic Acid → Benzhydrol

HRID 217549

Reaction equation

HRID 217549 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].CC(O)=O>C1COCC1>[C:9]1([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[OH:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3102BenzophenoneHCID 25517Ammonium Chloride

Product 1

HCID 7037Benzhydrol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 mmole (182 mg) of benzophenone dissolved in 5 mL THF was stirred with 0.5 g of 12% Li-AG and solid state proton sources such as NH4Cl, (NH4)2HPO4, or dropwise addition of glacial AcOH at room temperature after a deep blue colored solution is produced. The color of the reaction vessel gradually fades and becomes grey at the end indicating complete consumption of lithium. The reaction mixture was filtered, the solids washed with hexane, and the solvent was removed from the combined organic solutions under vacuum to obtain a white solid corresponding to diphenyl methanol as confirmed by 1H, 13C NMR and ESI-MS. See FIGS. 3A-3C.

Workup

  1. customis produced
  2. customconsumption of lithium
  3. filtrationThe reaction mixture was filtered
  4. washthe solids washed with hexane
  5. customthe solvent was removed from the combined organic solutions under vacuum

Sources & evidence

ORD record
ord-fec6cb85a6e2434088d9a39ed31a0e85
Source dataset
uspto-grants-2012_06
Patent number
US08197707B2

Linked notes

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