Benzophenone → Benzhydrol

HRID 1869605Notes

Reaction equation

HRID 1869605 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.[OH-].[Na+]>CC(O)C.C(C1C=CC=CC=1)(=O)C>[CH:1]([OH:8])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3102Benzophenone2×HCID 14798Sodium Hydroxide2×

Product 1

HCID 7037Benzhydrol

Reagents, catalysts & solvents 2

HCID 7410AcetophenoneCatalystHCID 3776IsopropanolSolvent3×

Procedure

1.8 g of benzophenone (10 mmol) and 45 ml of 2-propanol are introduced into a 100 ml flask under argon atmosphere. The system is heated under reflux. 2.5 ml of a 0.1 M solution of NaOH in 2-propanol and 2 ml of a 2-propanol solution containing the catalyst (10) (1.8 mg, 0.0025 mmol) are added. The molar ratios of benzophenone/catalyst/NaOH are equal to 4000/1/100. 1H NMR analysis of the mixture shows that the reaction is complete after 30 minutes. By evaporating the solvent, a colourless residue is obtained which is extracted with 30 ml of diethyl ether. This solution is then passed through a silica filled column to remove the catalyst and sodium hydroxide. The filtrate is dried by adding Na2SO4 and, after filtering and removal of the solvent, the benzhydrol is recovered and then dried under reduced pressure (10−2 mmHg).

Workup

  1. temperatureThe system is heated
  2. temperatureunder reflux
  3. additionare added
  4. customBy evaporating the solvent
  5. customa colourless residue is obtained which
  6. extractionis extracted with 30 ml of diethyl ether
  7. additionfilled column
  8. customto remove the catalyst and sodium hydroxide
  9. customThe filtrate is dried
  10. additionby adding Na2SO4
  11. filtrationafter filtering
  12. customremoval of the solvent
  13. customthe benzhydrol is recovered
  14. customdried under reduced pressure (10−2 mmHg)

Sources & evidence

ORD record
ord-f995339f48c04347a706b6bcdcc3019e
Source dataset
uspto-grants-2009_12
Patent number
US07638628B2

Reaction notes

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