Benzaldehyde → 1-Phenyl-1-propanol

HRID 1264157Notes

Reaction equation

HRID 1264157 reaction equation
C([Zn][CH2:4][CH3:5])C.[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCCCCC>[C:7]1([CH:6]([OH:13])[CH2:4][CH3:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 178418750HCID 178418750, compound

Product 1

HCID 71471-Phenyl-1-propanolYield 25%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 2.2 mL solution of diethylzinc in hexane, 0.2 mL of benzaldehyde and 2 mg of a mixture of compounds 6 and 7 was added. After 17 h, the reaction was quenched by the addition of a few drops of saturated ammonium chloride. Solvent extraction (CH2Cl2/H2O), followed by drying and evaporation of the organic solvent, and flash chromatography, resulted in the isolation of the addition product (1-phenyl-1-propanol) in 25% yield.

Workup

  1. customthe reaction was quenched by the addition of a few drops of saturated ammonium chloride
  2. extractionSolvent extraction (CH2Cl2/H2O)
  3. customby drying
  4. customevaporation of the organic solvent, and flash chromatography

Sources & evidence

ORD record
ord-5b92db595a2d4d34aab5f5da8888568b
Source dataset
uspto-grants-2003_04
Patent number
US06541628B1

Reaction notes

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