4-Hydroxybenzaldehyde → p-(2-(Dimethylamino)ethoxy)benzaldehyde

HRID 1663591Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-hydroxybenzaldehyde (2.0 g), dimethylaminoethyl chloride hydrochloride (2.83 g), dimethylformamide (8 mL) in diisopropylether (1 mL) is added potassium carbonate (5.53 g) and the mixture was stirred at 60° C. overnight. To the reaction mixture was added water and the mixture was extracted with ethyl acetate (×2). The organic layer is concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=100:0→90:10) to give 4-[2-(dimethylamino)ethoxy]benzaldehyde (674 mg, yield: 21%) as an oil.

Workup

extractionthe mixture was extracted with ethyl acetate (×2)
concentrationThe organic layer is concentrated in vacuo
customthe resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=100:0→90:10)

Sources & evidence

ORD record: ord-32d061b61ad746749d894872eb1fef99
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034949B2

Reaction notes

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