3-Hydroxybenzaldehyde → 3-(allyloxy)benzaldehyde

HRID 573514Notes

Reaction equation

HRID 573514 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[I-].[Na+].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH:13]=[CH2:12]

Participants

7

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 24436Sodium Sulfate

Product 1

HCID 27166123-(allyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1 L round bottomed flask equipped with mechanical stirrer, reflux condenser and thermometer was added in sequence 400 mL ethanol, 59.63 g of 3-hydroxybenzaldehyde (0.49 moles, 1 eq.), 7.3 g of sodium iodide (48 mmol, 0.1 eq.), 120.98 g of allyl bromide (0.59 moles, 1.2 eq.) and 101.6 g of potassium carbonate (0.74 moles, 1.25 eq.). The reaction mixture was heated to reflux and heating continued for three hours. Heating was then discontinued and the reaction was allowed to cool to room temperature. The mixture was then filtered through a Hyflosupercel pad and ethanol was removed by rotary evaporation. The residual oil was then taken up in 500 mL of MTBE and the organic phase washed sequentially with 10% aqueous sodium hydroxide, water and brine. After drying over sodium sulfate, filtration and rotary evaporation of solvent 79.7 g of a yellow oil of 3-allyloxybenzaldehyde (quantitative yield) was obtained.

Workup

  1. customIn a 1 L round bottomed flask equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperatureheating
  6. temperatureHeating
  7. filtrationThe mixture was then filtered through a Hyflosupercel pad and ethanol
  8. customwas removed by rotary evaporation
  9. washthe organic phase washed sequentially with 10% aqueous sodium hydroxide, water and brine

Sources & evidence

ORD record
ord-6c0415195842465ba8c102f211692451
Source dataset
uspto-grants-2015_05
Patent number
US09029607B2

Reaction notes

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