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

HRID 1725584Notes

Reaction equation

HRID 1725584 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 27644923-Methoxy-4-[(4-methoxyphenyl)methoxy]benzaldehydeYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzaldehyde (22.6 g, 149 mmol), 4-methoxybenzyl chloride (23.3 g, 149 mmol) and potassium carbonate (30.8 g, 223 mmol) was stirred in N,N-dimethylformamide (DMF) (150 mL) at 90 C for 2 hours. The solution was filtered hot, and cooled to room temperature. The filtrate was concentrated and dissolved ethyl acetate (300 mL) and extracted with aqueous sodium bicarbonate and water. The organics were dried with magnesium sulfate, filtered and concentrated. The crude product was recrystalized with ethyl acetate and hexanes to give product as an off-white solid (34.2 g, 126 mmol). 1H NMR (300 MHz, d6-DMSO): δ 9.86 (s, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.44-7.40 (m, 3H), 7.30 (d, J=8.4 Hz, 1H), 6.98 (d, J=8.7 Hz, 2H), 5.15 (s, 2H), 3.84 (s, 3H), 3.78 (s, 3H). MS (ES+, m/z)=273 (M+H).

Workup

  1. filtrationThe solution was filtered hot
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved ethyl acetate (300 mL)
  4. extractionextracted with aqueous sodium bicarbonate and water
  5. dry with materialThe organics were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystalized with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-bb4d26a59a30453c927d395d4d645b4f
Source dataset
uspto-grants-2009_02
Patent number
US07491731B2

Reaction notes

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