Allyl bromide → 2-allyloxy-4-methoxy-benzaldehyde

HRID 352345Notes

Reaction equation

HRID 352345 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 107978122-allyloxy-4-methoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 100 g of 2-hydroxy-4-methoxybenzaldehyde in 2 liters of acetone add 79.5 ml of allyl bromide and then, gradually, 272 g of potassium carbonate. Heat at reflux for 4 hours and then filter; concentrate the filtrate in vacuo, take up the residue in 1 liter of dichloromethane and wash the solution with 1N sodium hydroxide solution and then with saturated sodium chloride solution. Dry over magnesium sulphate and concentrate in vacuo.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 4 hours
  3. filtrationfilter
  4. concentrationconcentrate the filtrate in vacuo
  5. washwash the solution with 1N sodium hydroxide solution
  6. dry with materialDry over magnesium sulphate
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cf0ee0ed87244302bbe261a0fb02db05
Source dataset
uspto-grants-2004_06
Patent number
US06747032B2

Reaction notes

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