4-Hydroxybenzaldehyde → 4-(Allyloxy)benzaldehyde

HRID 1844238Notes

Reaction equation

HRID 1844238 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 959424-(Allyloxy)benzaldehydeYield 94.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of allyl bromide (5.94 mL, 68.78 mmol) in acetone (20 mL) was added, over a period of 20 min, to a mixture of 4-hydroxybenzaldehyde (8.00 g, 65.50 mmol) and K2CO3 (9.96 g, 72.06 mmol) in acetone (100 mL) cooled at 0° C. The mixture was allowed to reach room temperature and stirred for 60 h. After removal of the solvent, the crude residue was dissolved in EtOAc (100 mL) and washed twice with a mixture of water (100 mL) and NaOH (10% aqueous solution, 10 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, 10.00 g of 4-(allyloxy)benzaldehyde were obtained [Rf=0.5 (10% EtOAc/Hexanes), pale brown oil, 94% yield]

Workup

  1. customto reach room temperature
  2. customAfter removal of the solvent
  3. dissolutionthe crude residue was dissolved in EtOAc (100 mL)
  4. washwashed twice with a mixture of water (100 mL) and NaOH (10% aqueous solution, 10 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-538dba5a5d40482b8485cdf124f666a9
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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