Nitric Acid → 2-Nitro-5-(2-chloro-alpha,alpha,alpha-trifluoro-4-tolyloxy) benzoic acid

HRID 618471

Reaktionsgleichung

C(OC(=O)C)(=O)C.[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=[O:20])[CH:12]=[CH:11][C:10]=1[C:25]([F:28])([F:27])[F:26].S(=O)(=O)(O)O.[N+:34]([O-])([OH:36])=[O:35]>C(OCCCC)(=O)C>[N+:34]([C:22]1[CH:23]=[CH:24][C:16]([O:15][C:13]2[CH:12]=[CH:11][C:10]([C:25]([F:26])([F:27])[F:28])=[C:9]([Cl:8])[CH:14]=2)=[CH:17][C:18]=1[C:19]([OH:21])=[O:20])([O-:36])=[O:35]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Acetic anhydride (37.7 g) was added to 3-(2-chloro-α,α,α-trifluoro-4-tolyloxy)-benzoic acid (86% strength, 45 g) in n-butyl acetate (85.8 g) at 35° C. Sulphuric acid (98%, 12.2 g) was added slowly and the mixture cooled to 0° C. Nitric acid (90%, 10.4 g) was then added slowly over about 3 hours such that the temperature was maintained at -5 to 0° C. On completion of the nitric acid addition the reaction was quenched with water (60 g) at 0° C. The mixture was warmed to 50-60° C. and the aqueous layer removed. The solvent layer was washed with water (2×100 g) at 60° C. and the aqueous layer removed. The solvent and acetic acid were removed by distillation to give 2-nitro-5-(2-chloro-α,α,α-trifluoro-4-tolyloxy) benzoic acid (85%), 2'-nitro isomer (7.5 to 8.5 pph), total dinitro's (~0.5 pph).

Aufarbeitung

temperaturewas maintained at -5 to 0° C
customwas quenched with water (60 g) at 0° C
temperatureThe mixture was warmed to 50-60° C.
customthe aqueous layer removed
washThe solvent layer was washed with water (2×100 g) at 60° C.
customthe aqueous layer removed
customThe solvent and acetic acid were removed by distillation

Quellen und Nachweise

ORD-Eintrag: ord-08f7744ce4ec4e63976db311a0570b43
Quelldatensatz: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05952531

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