4-Hydroxybenzaldehyde → N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide

HRID 2082576Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:18]([O:20][C:21]([CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)=[O:22])[CH3:19].Cl>CN(C)C=O>[CH2:18]([O:20][C:21]([CH2:23][NH:24][C:25](=[O:28])[CH2:26][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:22])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4-hydroxybenzaldehyde (6.1 g), potassium carbonate (13.8 g), sodium iodide (0.75 g) and dimethylformamide (110 ml) was added N-(ethoxycarbonylmethyl)-2-chloroacetamide (8.9 g), and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was chromatographed on silica gel column (eluent; ethyl acetate), the desired fractions were collected and recrystallized from ethyl acetate/hexane to give N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.09 g).

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed successively with water
dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
customAfter evaporation of the solvent under reduced pressure
customthe residue was chromatographed on silica gel column (eluent; ethyl acetate)
customthe desired fractions were collected
customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-15d155aaf3b7414281c88d4742f907ef
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189211

Reaction notes

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