Hydrochloric Acid → 4-Cyano-3-nitrobenzoic acid

HRID 1943112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943112
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[OH-].[Na+].Cl>O1CCCC1.O>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:15])=[O:2])=[CH:5][C:6]=1[N+:12]([O-:14])=[O:13])#[N:11]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53419688Methyl 4-cyano-3-nitrobenzoate

Produkt 1

HCID 221685834-Cyano-3-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

4-Cyano-3-nitro-benzoic acid methyl ester (13.4 g, 61.6 mmol) was dissolved in tetrahydrofuran (74 ml) and aqueous sodium hydroxide (1M) (73.9 ml) was added. The reaction mixture was stirred at 25° C. for 4 hours. Then the reaction mixture was diluted with water (700 ml) and acidified with aqueous hydrochloric acid (1M). The mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. 4-Cyano-3-nitro-benzoic acid (12.0 g) was used in the next step without further purification. 1H-NMR (400 MHz, DMSO-d6): 13.00 (bs, 1H), 8.79 (s, 1H), 8.40 (d, 1H), 8.30 (d, 1H) ppm.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated
  4. custom4-Cyano-3-nitro-benzoic acid (12.0 g) was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-63532adad48e4395a51ba9fc5f66b21c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389766B2

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