2-Phenylethanol → (2-Allyloxyethyl)benzene

HRID 1734678Notes

Reaction equation

HRID 1734678 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:12](Br)[CH:13]=[CH2:14]>C1COCC1>[CH2:14]([O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 7841Allyl bromideHCID 24758Sodium hydride

Product 1

HCID 84328(2-Allyloxyethyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3x and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B.

Workup

  1. temperatureto warm to room temperature
  2. temperaturecooled
  3. customis brought to room temperature
  4. stirringstirred vigorously
  5. temperatureThe reaction mixture is heated at 45° C. for 3 hours
  6. customquenched with MeOH
  7. additiondiluted with Et2O
  8. washwashed with H2O 3x and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated to dryness
  11. customThe resultant yellow oil is purified by column chromatography

Sources & evidence

ORD record
ord-0d3fde4d0a874e93bbd7860ea049de1a
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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