1-Piperidinecarboxaldehyde → 2-Methoxybenzaldehyde

HRID 2221137Notes

Reaction equation

HRID 2221137 reaction equation
Br[CH2:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Mg]Cl)(C)C.[CH:15](N1CCCCC1)=[O:16]>O1CCCC1>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 13097734p-Bromo methoxybenzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 86582-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, treatment of the methoxybenzene (6a) with bromine in acetic acid in the presence of iron(0) provides the 2-bromomethoxybenzene (6c). Reaction of (6c) with isopropylmagnesium chloride and 1-formylpiperidine in a solvent such as tetrahydrofuran affords the 2-methoxybenzaldehyde (2d). Removal of the methyl group is accomplished by reaction of the 2-methoxybenzaldehyde (2d) with boron tribromide in a solvent such as dichloromethane to give the 2-hydroxybenzaldehyde (2c).

Sources & evidence

ORD record
ord-8951d7af2038423e93db964ef6f6ab59
Source dataset
uspto-grants-2008_05
Patent number
US07368477B2

Reaction notes

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