Sodium Iodide → HCID 56640302, compound

HRID 573516Notes

Reaction equation

HRID 573516 reaction equation
[CH2:1]([C:4]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[CH:2]=[CH2:3].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>CC(C)=O>[CH2:1]([C:4]1[C:11]([O:12][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 27751562-Allyl-3-hydroxybenzaldehyde

Product 1

HCID 56640302HCID 56640302, compoundYield 879.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 1 L three necked round bottom flask equipped with a mechanical stirrer, thermometer and reflux condenser was added 300 mL acetone, 23.19 g of 2-allyl-3-hydroxybenzaldehyde (0.143 mole, 1 eq.), 2.13 g of sodium iodide (14 mmol., 0.1 eq), 39.52 g of potassium carbonate (28.6 mmol., 2 eq.) and 22.39 g of p-methoxybenzyl chloride (14.3 mmol., 1 eq.). The reaction mixture was heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was filtered through a bed of Hyflosupercel and the solvent removed by rotary evaporation. The residual dark oil was taken up in 200 mL of toluene and washed sequentially with 10% aqueous sodium hydroxide, water and brine. The organic phase was dried over sodium sulfate and decolourized with 5 g Darco G60. After filtration through a Celite pad, the solvent was removed by rotary evaporation to give 35.5 g of oil which was then recrystallized from 175 mL of hot IPA. After cooling to room temperature and further cooling to 0-5° C., the solids were filtered and washed with IPA to afford after drying at 40° C., 24.74 g (61%) of 2-allyl-3-(4-methoxy-benzyloxy)-benzaldehyde as an off-white solid.

Workup

  1. temperaturethermometer and reflux condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 4 hours
  4. filtrationthe reaction mixture was filtered through a bed of Hyflosupercel
  5. customthe solvent removed by rotary evaporation
  6. washwashed sequentially with 10% aqueous sodium hydroxide, water and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationAfter filtration through a Celite pad
  9. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-41b74fe1fc3644c7a70992c9e5acfa5b
Source dataset
uspto-grants-2015_05
Patent number
US09029607B2

Reaction notes

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