Vanillin → HCID 23076519, compound

HRID 2221689Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[O:6][C:7]=1[CH3:8].[O:18]=[CH:19][C:20]1[CH:28]=[CH:27][C:25]([OH:26])=[C:22]([O:23][CH3:24])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:24][O:23][C:22]1[CH:21]=[C:20]([CH:28]=[CH:27][C:25]=1[O:26][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[O:6][C:7]=1[CH3:8])[CH:19]=[O:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloromethyl-5-methyl-2-(3-nitrophenyl)-1,3-oxazole (2.67 g), vanillin (1.52 g), anhydrous potassium carbonate (1.38 g) and N,N-dimethylformamide (30 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was dried over anhydrous magnesium sulfate, and filtered through a silica gel column. The filtrate was concentrated and the residue was washed with diethyl ether-hexane to give 3-methoxy-4-{[5-methyl-2-(3-nitrophenyl)-1,3-oxazol-4-yl]methoxy}benzaldehyde as colorless crystals (3.58 g, yield 97%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 179-180° C.

Workup

extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered through a silica gel column
concentrationThe filtrate was concentrated
washthe residue was washed with diethyl ether-hexane

Sources & evidence

ORD record: ord-59ec280948b34b27bce9b8604a356134
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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