Hydrochloric Acid → 6-Trifluoromethoxy-2H-chromene-3-carboxylic acid

HRID 1697458

Reaktionsgleichung

Reaktionsgleichung von HRID 1697458
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:8]([C:14]#N)=[CH:7]2.[OH-:18].[Na+].[OH2:20].Cl>>[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:8]([C:14]([OH:20])=[O:18])=[CH:7]2

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 669452446-Trifluoromethoxy-2H-chromene-3-carbonitrile

Produkt 1

HCID 581254866-Trifluoromethoxy-2H-chromene-3-carboxylic acid

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a microwave vial was added 6-trifluoromethoxy-2H-chromene-3-carbonitrile (100 mg, 0.4 mmol) and 10 M of sodium hydroxide in water (2 mL, 20 mmol). The reaction mixture was heated at 150° C. for 10 minutes in the microwave. The reaction mixture was acidified with conc. HCl then extracted with EtOAc (3×30 mL). The combined organics were washed with brine (3×30 mL), dried (MgSO4), filtered and concentrated, to give the product (42 mg) as a solid. m/z=258.9 (M−1), r.t.=3.43 mins. 1H NMR (400 MHz; CDCl3) δ 7.50 (1H, s), 7.11 (1H, dd), 7.04 (1H, d), 6.84 (111, d), 5.02 (2H, d).

Aufarbeitung

  1. extractionthen extracted with EtOAc (3×30 mL)
  2. washThe combined organics were washed with brine (3×30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7a9b1ff7ecaa413a8b6f2954c38feb94
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163901B2

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