Benzaldehyde → 1-Phenyl-1-propanol

HRID 496299Notes

Reaction equation

HRID 496299 reaction equation
[Zn](CC)[CH2:2][CH3:3].[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C1(C)C=CC=CC=1>[OH:13][CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 178418750HCID 178418750, compound

Product 1

HCID 71471-Phenyl-1-propanolYield 31.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(+)-Me-IAN amine (19.0 mg, 66.8 μmol) was dissolved in toluene (0.85 mL) in a 10 mL flask. Et2Zn (1.22 mL, 1.1 M in toluene, 1.34 mmol) was added in one portion via syringe. Immediately, a clear red-orange solution formed. After stirring for 30 min., benzaldehyde (0.068 mL, 0.669 mmol) was added. This addition immediately lightened the solution to a pale orange-yellow. After 19 h, the solution returned to its red-orange color. Water was added and the mixture was extracted three times with CH2Cl2. The combined organic phases were dried over MgSO4, filtered, and concentrated iii vacuo. Purification of the crude product via flash column chromatography on silica gel gave 1-hydroxy-1-phenylpropane as a light yellow liquid (28.6 mg, 31.4%). HPLC analysis of the product (OD column, 1.0 mL/min, 2% iPrOH in hexanes) gave 85.2% ee (retention time of major peak=13.7 min, retention time of minor peak=16.3 min) and a decrease in the ee of (+)-Me-IAN amine (from 99% to 93.2% ee).

Workup

  1. customImmediately, a clear red-orange solution formed
  2. additionThis addition
  3. waitAfter 19 h
  4. extractionthe mixture was extracted three times with CH2Cl2
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated iii vacuo
  8. customPurification of the crude product via flash column chromatography on silica gel

Sources & evidence

ORD record
ord-27b953a1ef8f4e8ba7c0d3340b9cf8b8
Source dataset
uspto-grants-2005_09
Patent number
US06943256B2

Reaction notes

Loading…