Methyl iodide → 4-Methoxy-3-(prop-2-en-1-yl)benzaldehyde

HRID 235613Notes

Reaction equation

HRID 235613 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH:2]=[CH2:3].[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 47290143-Allyl-4-hydroxybenzaldehyde

Product 1

HCID 176044904-Methoxy-3-(prop-2-en-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Two equivalents of potassium carbonate are added slowly with stirring to a solution of 4-hydroxybenzaldehyde in acetone. A solution of allyl bromide (1.1 equivalent) in acetone is added and the mixture is refluxed for two hours, filtered to remove inorganic salts and volatiles stripped under reduced pressure. The resulting 4-allyloxybenzaldehyde is then heated for six hours at 220° C. to yield the rearrangement product, 3-allyl-4-hydroxybenzaldehyde. One equivalent of 3-allyl-4-hydroxybenzaldehyde is dissolved in acetone and two equivalents of potassium carbonate are added slowly with stirring followed by a solution of 1.1 equivalents of methyl iodide in acetone. This mixture is refluxed for several hours, filtered and stripped to yield 3-allyl-4-methoxybenzaldehyde.

Workup

  1. temperatureThis mixture is refluxed for several hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-43ab34a04ed74de0a2bf16db3826d7ea
Source dataset
uspto-grants-1987_02
Patent number
US04640849

Reaction notes

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