3-Phenylprop-2-Enal → HCID 18177470, compound

HRID 394687Notes

Reaction equation

HRID 394687 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[CH:12](=[O:21])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>CN(C)C=O.O>[CH3:11][O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:13]([CH2:12][OH:21])=[CH:4]2

Participants

8

Reactant 5

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 18177470HCID 18177470, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.8 g (25 mmol) of 2-hydroxy-5-methoxybenzaldehyde are added to a solution of 3.63 g (27.5 mmol) of cinnamaldehyde in 25 ml of N,N-dimethylformamide; 3.8 g (27.5 mmol) of potassium carbonate are then added to the medium. After 10 minutes of reflux, the reaction mixture is concentrated in vacuo; the residue is then taken up in water. The aqueous phase is extracted with ethyl acetate; the organic phase is then dried over magnesium sulphate. After evaporation of the solvent in vacuo, the crude product is dissolved in 30 ml of anhydrous ethanol; 0.95 g (25 mmol) of sodium borohydride is then added to the medium. The solution is stirred under argon for 15 minutes; the solvent is then evaporated in vacuo. The residue obtained is dissolved in water and then hydrolysed with a 1N hydrochloric acid solution. The aqueous phase is extracted with ethyl acetate; the organic phase is then dried over magnesium sulphate. After evaporation of the solvent in vacuo, chromatography on a silica column (eluant: AcOEt/PE: 30/70 then 40/60) yields the title alcohol in the form of a yellow solid in a yield of 47%.

Workup

  1. temperatureAfter 10 minutes of reflux
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe organic phase is then dried over magnesium sulphate
  5. customAfter evaporation of the solvent in vacuo
  6. dissolutionthe crude product is dissolved in 30 ml of anhydrous ethanol
  7. customthe solvent is then evaporated in vacuo
  8. customThe residue obtained
  9. extractionThe aqueous phase is extracted with ethyl acetate
  10. dry with materialthe organic phase is then dried over magnesium sulphate
  11. customAfter evaporation of the solvent in vacuo, chromatography on a silica column (eluant

Sources & evidence

ORD record
ord-5c98580b2477486593199e95889909a5
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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