Vanillin → 4-(Hexyloxy)-m-anisaldehyde

HRID 1166008Notes

Reaction equation

HRID 1166008 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.Cl[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O>CS(C)=O.O>[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:17][C:16]1[CH:18]=[CH:19][C:11]([CH:10]=[O:9])=[CH:12][C:13]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 1183VanillinHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 15633624-(Hexyloxy)-m-anisaldehydeYield 84.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

41.45 g (300 mmol) of potassium carbonate and 27.4 g (165 mmol) of potassium iodide are added to a solution of 22.8 g (150 mmol) of vanillin and 30.7 g (225 mmol) of 6-chlorohexanol in 500 ml of dimethyl sulphoxide (DMSO) and the mixture is stirred overnight at 60° C. under nitiogen. The mixture is then cooled to room temperature, poured into 600 ml of water and extracted three times with 150 ml of ethyl acetate each time. The combined organic phases are washed twice with 200 ml of water each time, dried over magnesium sulphate, filtered and concentrated. Purification of the residue by chromatography on 400 g of silica gel using cyclohexane/ethyl acetate 1:1 yields 29.95 g of 4-(6-hexyloxy)-3-methoxybenzaldehyde.

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. extractionextracted three times with 150 ml of ethyl acetate each time
  3. washThe combined organic phases are washed twice with 200 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by chromatography on 400 g of silica gel

Sources & evidence

ORD record
ord-4107a0955c3d4f139bc725a5f734aac0
Source dataset
uspto-grants-2003_09
Patent number
US06613245B1

Reaction notes

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