Acetophenone → 2-Phenyl-4-penten-2-ol

HRID 2037388

Reaction equation

HRID 2037388 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[C:4]1([C:1]([OH:3])([CH2:12][CH:11]=[CH2:10])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 178455850HCID 178455850, compound

Product 1

HCID 1437612-Phenyl-4-penten-2-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetophenone (30 g, 0.25 mol) in dry THF (250 mL) at −78° C. was added dropwise 1M allylmagnesium bromide (1.25 L, 1.25 mol). After addition was complete, the mixture was allowed to stir at rt for 3 h. The reaction was quenched with satd aq NH4Cl solution (30 mL). The mixture was extracted with EtOAc (200 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to give 2-phenylpent-4-en-2-ol (40.2 g), which was used for the next step without purification.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched with satd aq NH4Cl solution (30 mL)
  3. extractionThe mixture was extracted with EtOAc (200 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05c76fb37542473ebc45980deadbda82
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Linked notes

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