Acetone → 2,4-Bis(allyloxy)benzaldehyde

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

Reactant 4

HCID 180Acetone

HCID 72132,4-Dihydroxybenzaldehyde

HCID 7841Allyl bromide

HCID 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.