Vanillin → HCID 6484658, compound

HRID 1405961Notes

Reaction equation

HRID 1405961 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][CH2:20][O:21][CH3:22].C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:19][CH2:20][O:21][CH3:22])[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 1183VanillinHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 6484658HCID 6484658, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methoxy-4-hydroxybenzaldehyde (8.0 g) in DMF (60 mL) was added K2CO3 (8.0 g) and 1-chloro-2-methoxyethane (5.1 g). The resulting mixture was stirred at 80° C. overnight. After reaction finished, ethyl acetate (200 mL) was added, and washed with 2 N aqueous HCl solution, brine, dried over Na2SO4, filtered, concentrated. The residue was washed with petrol ether to give 3-methoxy-4-(2-methoxyethoxy)benzaldehyde (10 g) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ: 9.86 (s, 1H); 7.45-7.41 (m, 2H); 7.01 (d, J=8.0, 1H); 4.27-4.25 (m, 2H); 3.93 (s, 3H); 3.85-3.82 (m, 2H); 3.46 (s, 3H).

Workup

  1. customAfter reaction
  2. washwashed with 2 N aqueous HCl solution, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with petrol ether

Sources & evidence

ORD record
ord-25a019342306431fad129e334974c6a2
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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