Water → p,p'-Dimethoxybenzhydryl alcohol

HRID 861914Notes

Reaction equation

HRID 861914 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.O>C(O)C>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([CH:9]([C:8]2[CH:19]=[CH:20][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[OH:10])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70324,4'-DimethoxybenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 69768p,p'-Dimethoxybenzhydryl alcoholYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.03 g of sodium borohydride was added to 4.84 g of 4,4'-dimethoxybenzophenone in 80 ml of ethanol, followed by stirring for 7 hours at room temperature. Next, after adding water and stirring for 30 minutes, the solution was concentrated to roughly 20 ml. Moreover, ethyl acetate and water were added and after extracting with ethyl acetate (50 ml×3), the product was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 4.84 g of the target compound. Yield: 99%

Workup

  1. stirringstirring for 30 minutes
  2. concentrationthe solution was concentrated to roughly 20 ml
  3. additionMoreover, ethyl acetate and water were added
  4. extractionafter extracting with ethyl acetate (50 ml×3)
  5. washthe product was washed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1c1fda0477074662ac8bbfd002fce594
Source dataset
uspto-grants-1998_02
Patent number
US05716958

Reaction notes

Loading…