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

HRID 2295897Notes

Reaction equation

HRID 2295897 reaction equation
[CH2:1]([OH:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O.CCOCC>ClCCl>[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 3283Diethyl EtherHCID 178526115HCID 178526115, compound

Product 1

HCID 3073-Phenylprop-2-Enal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 10 ml of dichloromethane is added 0.5 g. (3.73 mmoles) of cinnamyl alcohol. The resulting mixture is added to a stirred suspension of 3.37 g. (11.5 mmoles) of 2,2'-bipyridinium chlorochromate in 15 ml of dichloromethane. The resulting mixture is stirred for four hours after which 15 ml of anhydrous ether is added. The resulting product is filtered through a Hirsch funnel packed 1-2 cm deep with Celite® using ether as a wash solvent. The resulting clear filtrate is washed with 5% hydrochloric acid and 10% sodium carbonate, and dried over sodium sulfate. The drying agent is removed and the solvent evaporated giving a product which is a slightly yellow oil. This oil is then distilled via Kugelrohr to yield pure cinnamaldehyde in a typical yield of 0.323 g. which is 86% of theoretical yield.

Workup

  1. additionThe resulting mixture is added to a stirred suspension of 3.37 g
  2. additionis added
  3. filtrationThe resulting product is filtered through a Hirsch funnel
  4. washThe resulting clear filtrate is washed with 5% hydrochloric acid and 10% sodium carbonate
  5. dry with materialdried over sodium sulfate
  6. customThe drying agent is removed
  7. customthe solvent evaporated
  8. customgiving a product which
  9. distillationThis oil is then distilled via Kugelrohr

Sources & evidence

ORD record
ord-da69fbe193fb46888d6e9311ebcef5fa
Source dataset
uspto-grants-1984_01
Patent number
US04426534

Reaction notes

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