Benzaldehyde → 1-Phenyl-1-propanol

HRID 2185619Notes

Reaction equation

HRID 2185619 reaction equation
N1C=CC=CC=1O.C([Zn][CH2:11][CH3:12])C.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([CH:13]([OH:20])[CH2:11][CH3:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 178418750HCID 178418750, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 71471-Phenyl-1-propanol

Procedure

A dry Schlenk flask under argon was charged with 0.05 equiv. of the pyridinyl alcohol. The flask was evacuated twice and flushed with argon. Then, 5 mL of freshly distilled toluene were added followed by 1.5 equiv. of neat diethylzinc while stirred. After stirring for 20 min at room temperature, 1.0 equiv. of benzaldehyde (10) was added at the given temperature (see Table). The proceeding of the reaction was monitored by thin layer chromatograpy. After full conversion of the aldehyde, the reaction was quenched by careful addition of 10 mL of 2 M HCl, and the resulting mixture was extracted three times with 25 mL of dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, hexane/methyl tert-butylether=10:1) followed by Kugelrohr distillation to give 1-phenylpropanol (11) as a colorless oil. The enantiomeric excess of 11 was determined by HPLC on a stationary phase [CHIRALCEL OD, n-heptane/iso-propanol=98:2, 1 0 mL/min; tR=17.2 min (R); 21.5 min (S)], and the absolute configuration was determined by correlation of the optical rotation with the values reported in the literature (Soai, K.; Ookawa.; Kaba, T.; Ogawa, K.; J. Arn. Chem. Soc. 1987, 109, 7111).

Workup

  1. customThe flask was evacuated twice
  2. customflushed with argon
  3. additionThen, 5 mL of freshly distilled toluene were added
  4. stirringAfter stirring for 20 min at room temperature
  5. customAfter full conversion of the aldehyde, the reaction was quenched by careful addition of 10 mL of 2 M HCl
  6. extractionthe resulting mixture was extracted three times with 25 mL of dichloromethane
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. customthe solvent was removed under reduced pressure
  10. customThe crude product was purified by column chromatography (silica gel, hexane/methyl tert-butylether=10:1)
  11. distillationfollowed by Kugelrohr distillation

Sources & evidence

ORD record
ord-eb2948c9e1ed49f187b464dadf48ca18
Source dataset
uspto-grants-2002_06
Patent number
US06403522B1

Reaction notes

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