Salicylaldehyde → 2-(3,5-Dimethoxybenzyloxy)benzaldehyde

HRID 1976210Notes

Reaction equation

HRID 1976210 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].BrC[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[O:20][CH3:21].[C:22](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:19][O:18][C:15]1[CH:16]=[C:17]([CH:12]=[C:13]([O:20][CH3:21])[CH:14]=1)[CH2:22][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

Product 1

HCID 220006772-(3,5-Dimethoxybenzyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Salicylaldehyde (0.32 cm3, 3.00 mmol), 4-bromomethyl-1,3-dimethoxybenzene (0.63 g, 2.73 mmol), potassium carbonate (0.42 g, 3.00 mmol), and 18-crown-6-ether (0.07 g, 0.27 mmol) were stirred together at room temperature in acetone (50 cm3, 99%) under nitrogen for 18 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (20 cm3) and water (20 cm3). The aqueous layer was extracted with dichloromethane (2×20 cm3), and the combined extracts were washed with water (2×50 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane:ethyl acetate, 5:1) to give a white crystalline solid. The solid was recrystallized from heptane and ethyl acetate to give the ether, (0.58 g, 78%), as white fibrous needles, mp 68-69° C.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (2×20 cm3)
  3. washthe combined extracts were washed with water (2×50 cm3)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed (SiO2, heptane:ethyl acetate, 5:1)
  7. customto give a white crystalline solid
  8. customThe solid was recrystallized from heptane and ethyl acetate
  9. customto give the ether, (0.58 g, 78%)

Sources & evidence

ORD record
ord-289d003fae6a4932b41acf239015f16e
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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