Vanillin → 2-Phenoxyacetamide

HRID 1820006Notes

Reaction equation

O[C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][C:3]=1[O:10][CH3:11].BrC[C:14]([NH:16]C1C=CC(Br)=CC=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].C(#N)CC>C(OCC)(=O)C>[O:10]([CH2:11][C:14]([NH2:16])=[O:15])[C:3]1[CH:2]=[CH:9][CH:8]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-hydroxy-3-methoxybenzaldehyde (2.02 g, 13.3 mmol), 2-bromo-N-(4-bromophenyl)acetamide (3.00 g, 10.2 mmol) and potassium carbonate (2.12 g, 15.4 mmol) was added propionitrile (10 ml), and the mixture was stirred at 80° C. for one day. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate), and powderized with ethyl acetate-diisopropyl ether (1:5) to give a phenoxyacetamide derivative (2.93 g). The title compound was obtained by similar operations as in Reference Example 43 and Example 6 and using this compound.

Workup

washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record: ord-a87d2fb6c4d143778be2bab68757a9a6
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601868B2

Reaction notes

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