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

Participants

Reaction Conditions

Reaction Steps

3-Chloropropyltrimethylsilane (33.14 g, 0.22 mol) is added dropwise, over 10 minutes, to a mixture of 4-hydroxybenzaldehyde (24.4 g, 0.2 mol) and of potassium carbonate (30.4 g, 0.22 mol) in 150 ml of dry DMF heated to 120° C. under nitrogen. The reaction mixture is left for 2 hours 30 minutes at 120–130° C. It is cooled and poured into ice-cold water. The aqueous phase is extracted 3 times with dichloromethane. The organic phases are dried over sodium sulfate and concentrated under vacuum. After vacuum distillation (0.2 mmHg), 40.5 g (yield: 86%) of 4-(3-trimethylsilanylpropyloxy)benzaldehyde are obtained in the form of a colorless oil which distils at 110–114° C. and which is used as it is in the next step.

Provenance & Evidence