Dihydrochalcone → 1,3-Diphenylpropan-1-ol

HRID 363014

Reaction equation

HRID 363014 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:11]1([CH:9]([OH:10])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 64802DihydrochalconeHCID 4311764Sodium borohydride

Product 1

HCID 2501291,3-Diphenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

β-Phenylpropiophenone (6-1) (7.5 g, 36.0 mmol) was suspended in ethanol (100 ml) and sodium borohydride (0.68 g, 18.0 mmol) was added under N2. The resulting solution was stirred at ambient temperature overnight. The ethanol was removed in vacuo and the residual oil-solid was taken up in ethyl acetate (100 ml) and water (30 ml). The ethyl acetate layer was removed, washed with water, dried, filtered and concentrated in vacuo to give 6-2 as a colorless oil.

Workup

  1. customThe ethanol was removed in vacuo
  2. customThe ethyl acetate layer was removed
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f650809c4e84eedb17aac34a747ef24
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Linked notes

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