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

HRID 352345
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747032B2

Reaction notes

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