Vanillin → 3-Methoxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

HRID 1951967Notes

Reaction equation

HRID 1951967 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[O:26][CH3:27]>CC(C)=O.CCCCCCC>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:18]=1[O:17][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH:22]=[O:23]

Participants

6

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 27644923-Methoxy-4-[(4-methoxyphenyl)methoxy]benzaldehydeYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
55 °C

Procedure

5 g (36.1 mmol) of potassium carbonate and then 4.9 ml (36.1 mmol) of 1-chloromethyl-4-methoxy-benzene are added to a solution of 5 g (33 mmol) of 4-hydroxy-3-methoxy-benzaldehyde in 100 ml of acetone. The reaction mixture is then stirred at 55° C. for 28 hours and then filtered. The filtrate is concentrated under vacuum. The residue obtained is taken up in heptane and filtered. 8.9 g (100%) of 3-methoxy-4-(4-methoxy-benzyloxy)-benzaldehyde is obtained in the form of a beige solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under vacuum
  3. customThe residue obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-43fe7caa76d942678f269dbe2dedd8f9
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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