Vanillin → 3-Methoxy4-(3-trimethylsilanylpropyloxy)benzaldehyde

HRID 2230925Notes

Reaction equation

HRID 2230925 reaction equation
Cl[CH2:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[O:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][O:14][C:13]1[CH:12]=[C:11]([CH:19]=[CH:18][C:16]=1[O:17][CH2:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])[CH:10]=[O:9]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 75362(3-Chloropropyl)trimethylsilane

Product 1

HCID 184631723-Methoxy4-(3-trimethylsilanylpropyloxy)benzaldehydeYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-Chloropropyltrimethylsilane (33.14 g, 0.22 mol) was added dropwise over the course of 20 minutes into a mixture of vanillin (30.4 g, 0.2 mol) and potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry dimethylformamide (DMF) heated to 50° C. under nitrogen. The mixture was maintained for 4 hours at 95°-110° C. The reaction mixture was cooled and poured into ice water. The aqueous phase was extracted 3 times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated in vacuo. After distillation in vacuo (0.04 mm Hg), 47.5 g (yield: 89%) of 3-methoxy4-(3-trimethylsilanylpropyloxy)benzaldehyde were obtained in the form of a slightly pink oil distilling at 112°-114° C. and employed as such in the following step (b).

Workup

  1. temperatureThe mixture was maintained for 4 hours at 95°-110° C
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aqueous phase was extracted 3 times with dichloromethane
  4. dry with materialThe organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationAfter distillation in vacuo (0.04 mm Hg)

Sources & evidence

ORD record
ord-a66bf718f9584db2b028a7bd0f7f20bc
Source dataset
uspto-grants-2002_07
Patent number
US06426428B2

Reaction notes

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