Water → Methyl 2-chlorodibenzo[b,f]oxepin-11-carboxylate

HRID 1970104

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:21])[C:4]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:5]O.CCCCCC.C1(C)C=CC=CC=1.O>P(OP(O)(O)=O)(O)(O)=O>[CH3:1][O:2][C:3]([C:4]1[C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:5]=1)=[O:21]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A slurry of 2-(5-chloro-2-phenoxy-phenyl)-3-hydroxy-acrylic acid methyl ester (210 g, 691 mmol) was heated in pyrophosphoric acid (420 g) to 60° C. After two hours, the reaction was cooled to 20° C. and hexane (250 mL), toluene (500 mL), and water (500 mL) were added to quench the reaction. The organic layer was separated and washed with saturated aqueous sodium bicarbonate (500 mL) and saturated brine (500 mL). The organic fraction was concentrated and the resulting oil was crystallized from n-butanol (500 mL; 20° C. for one hour and −10° C. for two hours), which provided the titled compound as off-white crystals (172 g, 85% yield for steps A and B). 1H NMR (400 MHz, CDCl3) 3.9 (s, 3H), 7.1-7.2 (m, 3H), 7.3 (m, 2H), 7.4 (t, 1H), 7.6 (d, 1H), 8.0 (s, 1H).

Aufarbeitung

customto quench
customthe reaction
customThe organic layer was separated
washwashed with saturated aqueous sodium bicarbonate (500 mL) and saturated brine (500 mL)
concentrationThe organic fraction was concentrated
customthe resulting oil was crystallized from n-butanol (500 mL; 20° C. for one hour and −10° C. for two hours), which

Quellen und Nachweise

ORD-Eintrag: ord-c2c2ea9c52f649e39657d96d689d23d4
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08426610B2

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