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

HRID 427196Notes

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=O)C>[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

Conditions

Temperature: 80 °C

Procedure

3-chloropropyltrimethylsilane (33.14 g, 0.22 mol) was added dropwise over 20 minutes to a mixture of vanillin (30.4 g, 0.2 mol) and potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry DMF heated to 80° C. under nitrogen. The mixture was maintained for 4 hours at 95°-110° C. The reaction mixture was cooled and poured into ice-cold water. The aqueous phase was extracted three times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated under vacuum. After distillation under vacuum (0.04 mm Hg), 47.5 g (yield: 89%) of 3-methoxy-4-(3-trimethylsilanylpropyloxy) benzaldehyde were obtained in the form of a slightly pinkish oil distilling at 112°-114° C. and employed without further purification in the following step.

Workup

temperatureThe mixture was maintained for 4 hours at 95°-110° C
temperatureThe reaction mixture was cooled
additionpoured into ice-cold water
extractionThe aqueous phase was extracted three times with dichloromethane
dry with materialThe organic phases were dried over sodium sulfate
concentrationconcentrated under vacuum
distillationAfter distillation under vacuum (0.04 mm Hg)

Sources & evidence

ORD record: ord-706f3851e3ca4ff38ca96cc8e02274b9
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06312673B2

Reaction notes

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