4-Hydroxybenzaldehyde → 4-(3-Trimethylsilanylpropyloxy)benzaldehyde

HRID 427197Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

3-chloropropyltrimethylsilane (33.14 g, 0.22 mol) was added dropwise over 10 minutes to a mixture of 4-hydroxybenzaldehyde (24.4 g, 0.2 mol) and potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry DMF maintained at 120° C. under nitrogen. The mixture was maintained for 2 hours, 30 minutes, at 120°-130° C. The reaction mixture was cooled and poured into ice-cold water. The aqueous phase was extracted 3 times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated under vacuum. After distillation under vacuum (0.2 mmHg), 40.5 g (yield: 86%) of 4-(3-trimethylsilanylpropyloxy) benzaldehyde were obtained in the form of a colorless oil distilling at 110-114° C. and employed without further purification in the following step.

Workup

temperatureThe mixture was maintained for 2 hours, 30 minutes, at 120°-130° C
temperatureThe reaction mixture was cooled
additionpoured into ice-cold water
extractionThe aqueous phase was extracted 3 times with dichloromethane
dry with materialThe organic phases were dried over sodium sulfate
concentrationconcentrated under vacuum
distillationAfter distillation under vacuum (0.2 mmHg)

Sources & evidence

ORD record: ord-78de7a58c1ca41efb0637ee822403093
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06312673B2

Reaction notes

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