4-Hydroxybenzaldehyde → 4-Trimethylsilanylmethoxybenzaldehyde

HRID 899016Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Chloromethyltrimethylsilane (110.5 g, 0.9 mol) is added dropwise over 30 minutes to a mixture of para-hydroxybenzaldehyde (110 g, 0.82 mol) and potassium carbonate (124.5 g, 0.9 mol) in 1 L of dry DMF maintained at 80° C., and while sparging with nitrogen. The mixture is left at 90° C. for 4 hours. The reaction mixture is filtered and the solvent is removed from the filtrate by distillation under vacuum. The final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg. 142.4 g (yield: 84%) of 4-trimethylsilanylmethoxybenzaldehyde are obtained in the form of an orange-yellow oil, which is used without further purification in the next step.

Workup

customwhile sparging with nitrogen
filtrationThe reaction mixture is filtered
customthe solvent is removed from the filtrate by distillation under vacuum
customThe final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg

Sources & evidence

ORD record: ord-dfab117446f04b698ae0f92944dbd878
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354571B2

Reaction notes

Loading…