Acetone → 2,4-BIS(ALLYLOXY)BENZALDEHYDE

HRID 394960Notes

Reaction equation

HRID 394960 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]([CH3:24])=O>>[CH2:12]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:24][CH:22]=[CH2:21])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH:13]=[CH2:14]

Participants

5

Reactant 4

HCID 180AcetoneHCID 72132,4-DihydroxybenzaldehydeHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 51824082,4-BIS(ALLYLOXY)BENZALDEHYDEYield 93%

Procedure

To a solution of 6.9 g (50 mmol) of 2,4-dihydroxybenzaldehyde in 100 ml of acetone was added 12 ml (120 mmol) of 3-bromopropene and 40 g of potassium carbonate and the mixture was refluxed for 3 h under stirring. The mixture was filtered and the filtrate concentrated in vacuo to give 10.2 g (93%) of 2,4-diprop-2-enyloxybenzaldehyde as slightly reddish crystals.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-b4afe83461064144a8ba926fc5539048
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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