Benzenepropanal → HCID 9834042, compound

HRID 654932Notes

Reaction equation

HRID 654932 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[C:5]1([CH2:11][CH2:12][CH:13]=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCCC1>[C:5]1([CH2:11][CH2:12][CH:13]([OH:14])[CH:1]=[CH2:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 178418507HCID 178418507, compound

Product 1

HCID 9834042HCID 9834042, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To vinyl magnesium bromide (550 ml of a 1.0M solution) was added 3-phenylpropionaldehyde (36.68 g, 0.273 mol) in tetrahydrofuran (300 ml) under argon at 0°. This mixture was stirred for one hour at room temperature, quenched with aqueous ammonium chloride and ice, and extracted into ethyl ether. The organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol which was carried on without further purification.

Workup

  1. customquenched with aqueous ammonium chloride and ice
  2. extractionextracted into ethyl ether
  3. washThe organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3bf74806670243e7ae02c56c2a19054e
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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