Potassium Permanganate → 7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid

HRID 1518022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518022
[O-:1][Mn](=O)(=O)=O.[K+].[F:7][C:8]1[C:9]([CH:18]=[O:19])=[CH:10][C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1>O>[F:7][C:8]1[C:9]([C:18]([OH:1])=[O:19])=[CH:10][C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1

Komponenten

4

Edukt 2

HCID 516875Potassium PermanganateHCID 146448837-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde

Produkt 1

HCID 595606017-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acidAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of KMnO4 (0.35 g, 2.2 mmol) in H2O (11 mL) at 80° C. was added 7-fluoro-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde (0.20 g, 1.1 mmol). The resulting suspension was stirred at 100° C. for 24 h. The reaction mixture was filtered and the solids were washed with H2O (30 mL). The filtrate was acidified with concentrated HCl, which led to the formation of a white precipitate, which was collected, washed with H2O and dried in vacuo to provide 0.12 g (57%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7FO4, 198.03; m/z not found. 1H NMR (400 MHz, DMSO-d6): 12.95 (s, 1H), 7.29 (d, J=7.2, 1H), 6.87 (d, J=11.6, 1H), 4.34-4.31 (m, 2H), 4.27-4.24 (m, 2H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with H2O (30 mL)
  3. customwas collected
  4. washwashed with H2O
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e590d7aed2c54e888f55d9ac4b768d08
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232391B2

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