Chlorotrimethylsilane → Methyl 4-Formylbenzoate

HRID 1828669Notes

Reaction equation

HRID 1828669 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:12][Si](Cl)(C)C>CO>[CH3:12][O:2][C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 120884-Formylbenzoic acid

Product 1

HCID 15294Methyl 4-Formylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 4-carboxybenzaldehyde is of commercial origin. It is dissolved (3 g; 20 mmol) in a trimethylsilyl chloride solution (10 g; 92 mmol) in 100 ml of MeOH. The mixture is kept stirred for 40 h at room temperature. After evaporation, a white solid corresponding to 4-methoxycarbonylbenzaldehyde 24 is isolated, characterized by NMR and used as it is for the next reaction.

Workup

  1. customAfter evaporation

Sources & evidence

ORD record
ord-4285c4f31494403c9ef411010f07e532
Source dataset
uspto-grants-2006_06
Patent number
US07060441B2

Reaction notes

Loading…