Vanillin → 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde

HRID 131271Notes

Reaction equation

HRID 131271 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 1183VanillinHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 8746213-Methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of vanilin (76.1 g) in N,N-dimethylformamide (500 mL) is added successively 4-(2-chloroethyl)morpholine hydrochloride (130 g), sodium iodide (7.5 g), and potassium carbonate (207 g). The mixture is stirred at 80° C. for 15 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. To the residue is added diisopropyl ether and the resultant crystals are collected by filtration to give 3-methoxy-4-(2-morpholinoethoxy)-benzaldehyde (112.6 g, yield; 85%) as orange crystals. MS (APCI) m/z: 266 [M+H]+

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionTo the residue is added diisopropyl ether
  7. filtrationthe resultant crystals are collected by filtration

Sources & evidence

ORD record
ord-061c5ac602954d358e09e4c3aad3133d
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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