Benzophenone → Benzhydrol

HRID 1915027Notes

Reaction equation

HRID 1915027 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.O(C(C)C)[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 178459997HCID 178459997, compound2×

Product 1

HCID 7037Benzhydrol

Reagents, catalysts & solvents 2

HCID 7410AcetophenoneCatalystHCID 3776IsopropanolSolvent3×

Procedure

1.82 g of benzophenone (10 mmol) and 98 ml of 2-propanol were added to a 100 ml flask under argon atmosphere and heated to reflux. A 0.1 M NaOiPr solution in 2-propanol (2 ml) and 400 μl of a 2-propanol solution containing the catalyst (7) (3 mg, 0.0039 mmol dissolved in 8 ml of 2-propanol) were added. The molar ratios of benzophenone/catalyst/NaOiPr were equal to 50000/1/1000. 1H NMR analysis of the mixture indicated that the reaction was complete after 2 hours. By evaporating the solvent, a colourless residue was obtained which was extracted with 30 ml of diethyl ether. This solution was then passed through a silica filled column to remove the catalyst and sodium alkoxide. The filtrate was treated with Na2SO4, filtered, and removal of the solvent led to benzhydrol which was dried under reduced pressure (10−2 mmHg).

Workup

  1. temperatureheated to reflux
  2. additionwere added
  3. customBy evaporating the solvent
  4. customa colourless residue was obtained which
  5. extractionwas extracted with 30 ml of diethyl ether
  6. additionfilled column
  7. customto remove the catalyst and sodium alkoxide
  8. additionThe filtrate was treated with Na2SO4
  9. filtrationfiltered
  10. customremoval of the solvent
  11. customwas dried under reduced pressure (10−2 mmHg)

Sources & evidence

ORD record
ord-62c03dc1a6ad44ccb809d4d3a9a3b5c8
Source dataset
uspto-grants-2013_12
Patent number
US08614322B2

Reaction notes

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