Benzoic Acid → 6-Bromo-2-(4-nitrophenyl)-1,3-benzodioxan

HRID 248805

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].C(O)(=O)C1C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:18]([C:17]3[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=3)[O:8][CH2:7][C:6]=2[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

An intimately ground mixture of 5-bromo-2hydroxybenzyl alcohol (4.06 g), 4-nitrobenzaldehyde (3.93 g) and benzoic acid (0.2 g) was stirred and heated to 85° C. (±5° C.) under nitrogen for 88 hours. The clear melt which formed initially gradually solidified throughout the reaction period. The resulting solidified mass was cooled and dissolved in ethyl acetate (250 ml). The solution was then washed with 20% aqueous sodium carbonate, 20% aqueous sodium bisulphite and finally with brine. After drying over sodium sulphate, the organic phase was evaporated to yield a solid residue which was purified by briefly suspending in hot ethanol (approx. 75 ml) and cooling to 0°-5° C. The pure product was obtained as pale buff-coloured crystals (4.69g, 70%), mp 163°-164° C.

Aufarbeitung

customThe clear melt which formed initially gradually
customsolidified throughout the reaction period
temperatureThe resulting solidified mass was cooled
washThe solution was then washed with 20% aqueous sodium carbonate, 20% aqueous sodium bisulphite and finally with brine
dry with materialAfter drying over sodium sulphate
customthe organic phase was evaporated
customto yield a solid residue which
customwas purified
temperaturecooling to 0°-5° C

Quellen und Nachweise

ORD-Eintrag: ord-246961ac753c41a7b1297a7ca94aeffc
Quelldatensatz: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05212171

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