3-Phenylprop-2-En-1-Ol → 3-Phenylprop-2-Enal

HRID 48550

Reaction equation

HRID 48550 reaction equation
[CH2:1]([OH:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[N+](C1C=CC=CC=1C=O)([O-])=O.Cl>C1C=CC=CC=1.C(OCC)(=O)C>[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 3083-Phenylprop-2-En-1-OlHCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 11143Aluminum isopropoxide

Product 1

HCID 3073-Phenylprop-2-EnalYield 98.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cinnamyl alcohol (270 mg, 2.0 mmol) was dissolved in benzene (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.20 mmol) and 2-nitrobenzaldehyde (390 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and made acidic with addition of 2 N hydrochloric acid, and then the organic layer was separated. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 260 mg (yield: 97%) of the title compound as yellow oil.

Workup

  1. customthe organic layer was separated
  2. washSubsequently, the organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-e0be993750554c2e8d74cf2b7b4f6647
Source dataset
uspto-grants-2004_03
Patent number
US06703527B2

Linked notes

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