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4-Hydroxybenzaldehyde → 4-Trimethylsilanylmethoxybenzaldehyde

HRID 899016
Notes
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Reaction equation

HRID 899016 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 565289644-TrimethylsilanylmethoxybenzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customwhile sparging with nitrogen
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent is removed from the filtrate by distillation under vacuum
  4. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes