(+)-Styrene oxide → (+)-2-Phenyl-1-propanol

HRID 2085449Notes

Reaction equation

HRID 2085449 reaction equation
[CH3:1][Al](C)C.[CH2:5]1[O:7][C@@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[C:8]1([C@@H:6]([CH3:1])[CH2:5][OH:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 114705(+)-Styrene oxideHCID 16682925Trimethylaluminum

Product 1

HCID 177050(+)-2-Phenyl-1-propanolYield 92.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-60 °C

Procedure

An oven dried 500.0 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel with a continuous nitrogen blanket is charged with 2.0 M solution of trimethylaluminum (65.6 mL, 131.2 mmol) and toluene (75.0 mL). Reaction solution was then chilled to −60° C. with dry ice/acetone bath. To this solution was then added R-styrene oxide dissolved in 100.0 mL of toluene over a period of 50.0 minutes (reaction is quite exothermic and can be controlled by the rate of addition of substrate). After stirring at this temperature for 60.0 minutes, reaction was brought to room temperature and stirred for 4.0 hours. Reverse quenched reaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (quenching was quite exothermic with evolution of gas). Filtered the precipitate formed over hyflo, then concentrated filtrate to provide the intermediate title compound, (2R)-2-phenylpropan-1-ol, (11.03 g, 92.6%) as an oil; 1H nmr (CDCl3, 300 MHz) δ 1.28-1.29 (d, 3H, J=6.9Hz), 1.5 (b, 1H), 2.9-3.0 (m, 1H), 3.69-3.70 (d, 2H, J=6.64Hz), 7.24-7.35 (aromatic); 1 nmr (CDCl3, 300 MHz) δ 18.31, 43.15, 69.40, 127.38, 128.20, 129.26144.39.

Workup

  1. dry with materialAn oven dried 500.0 mL three necked round bottom flask
  2. customequipped with a mechanical stirrer
  3. additionthermometer, addition funnel with a continuous nitrogen blanket
  4. customReaction solution
  5. customreaction
  6. additioncan be controlled by the rate of addition of substrate)
  7. customreaction
  8. customwas brought to room temperature
  9. stirringstirred for 4.0 hours
  10. customReverse quenched
  11. customreaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (
  12. customquenching
  13. filtrationFiltered the precipitate
  14. customformed over hyflo

Sources & evidence

ORD record
ord-59a105deca85474ea739bac3df72a4a7
Source dataset
uspto-grants-2004_04
Patent number
US06720357B2

Reaction notes

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