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Hydrochloric Acid → 6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 855006
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:25])([F:24])[F:23])[C:6]([C:26]([O:28]CC)=[O:27])=[CH:5]2.O.[OH-].[Li+].[Al].Cl>C(OCC)C.C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:24])([F:25])[F:23])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2
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Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 5359268AluminumHCID 69518202ethyl 6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 114873096-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acidAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the concd product of step 1 in a suitable vial was added 400 mg (mmole) of lithium hydroxide monohydrate, 1 mL of water, 2 mL of methanol and 7 mL of THF. The vial was capped, in an aluminum heating block and the block heated to 100° C. for 30 min. After allowing the vial to cool to rt, the mixture was treated with 5 mL of 1N HCl and 2 mL of diethyl ether. The organic layer was removed and the aqueous layer extracted two times with diethyl ether. Combined organic extracts were concd by evaporation of solvent under a stream of N2 followed by conc in vacuo to afford 150 mg (34.6%) of a yellow solid: 1H NMR (CDCl3/300 MHz) 2.26 (s, 3H), 5.64 (q, 1H, J=6.8 Hz), 6.27 (s, 1H), 6.94 (s, 1H), 7.26 (s, 1H), 7.3H (s, 1H), 11.28 (hs, 1H); MS (ES−) 431 (M−1, 100); HRMS (ES−) m/z calcd for (M−H; C19H12Cl2F3O4) 431.0059, found 431.0048.

Aufarbeitung

  1. temperatureto cool to rt
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted two times with diethyl ether
  4. customCombined organic extracts were concd by evaporation of solvent under a stream of N2

Quellen und Nachweise

ORD-Eintrag
ord-f034ea96a5b345dea9a765ca46c4cf98
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07259266B2

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