Potassium Carbonate → 3-(2-Benzyloxyethoxy)-4-methoxy-benzaldehyde

HRID 1289019Notes

Reaction equation

HRID 1289019 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[CH2:12]([O:19][CH2:20][CH2:21]I)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[CH2:12]([O:19][CH2:20][CH2:21][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 103553141-Benzyloxy-2-iodoethane

Product 1

HCID 217163293-(2-Benzyloxyethoxy)-4-methoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

20 g isovanillin (Formula IIIa), 41.3 g 2-benzyloxyethyl iodide (Formula IIIb) and 21.8 g potassium carbonate in 200 ml ethyl methyl ketone are stirred for 12 hrs. under reflux. The obtained suspension is cooled to room temperature and the precipitate filtered off, washed with acetone and evaporated. The residue is taken up in ethyl acetate and extracted with H2O (3×) and brine (1×). The organic phase is dried, filtered and evaporated to yield the title compound as an oil.

Workup

  1. temperatureunder reflux
  2. filtrationthe precipitate filtered off
  3. washwashed with acetone
  4. customevaporated
  5. extractionextracted with H2O (3×) and brine (1×)
  6. customThe organic phase is dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-95595702d86540118f63b1054a62fb82
Source dataset
uspto-grants-1998_05
Patent number
US05747506

Reaction notes

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