Potassium hydroxide monohydrate → 4-Hydroxy-6-chloro-8-trifluoromethoxychroman-4-yl carboxylic acid

HRID 1294479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294479
[OH:1][C:2]1([C:18]([O:20]C)=[O:19])[C:11]2[C:6](=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=[C:9]([Cl:12])[CH:10]=2)[O:5][CH2:4][CH2:3]1.[OH-].[K+].O>C(O)(C)C>[OH:1][C:2]1([C:18]([OH:20])=[O:19])[C:11]2[C:6](=[C:7]([O:13][C:14]([F:17])([F:15])[F:16])[CH:8]=[C:9]([Cl:12])[CH:10]=2)[O:5][CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 23719240Potassium hydroxide monohydrateHCID 86615847HCID 86615847, Verbindung

Produkt 1

HCID 227083424-Hydroxy-6-chloro-8-trifluoromethoxychroman-4-yl carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxy-6-chloro-8-trifluoromethoxychroman-4-yl carboxylic acid, methyl ester in iso-propanol (50 mL) was added to KOH/H2O (20%, 60 mL) and the mixture was refluxed overnight. The resultant solution was partially concentrated, and the remainder was acidified with H2SO4 (10%). The very turbid mixture was extracted with ether (3×), and the combined organic phase was dried (Na2SO4) and concentrated. The crude product was purified via prep-HPLC (CH3CN:0.1M ammonium acetate (30:60)). The fractions of interest were partly concentrated and extracted with ether. The combined organic layers were washed with water, dried (Na2SO4), and concentrated, yielding 0.24 g (10% over steps (vi)–(ix)).

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. concentrationThe resultant solution was partially concentrated
  3. extractionThe very turbid mixture was extracted with ether (3×)
  4. dry with materialthe combined organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified via prep-HPLC (CH3CN:0.1M ammonium acetate (30:60))
  7. concentrationThe fractions of interest were partly concentrated
  8. extractionextracted with ether
  9. washThe combined organic layers were washed with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customyielding 0.24 g (10% over steps (vi)–(ix))

Quellen und Nachweise

ORD-Eintrag
ord-3791df1d48984dd887b850861a79aae0
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241757B2

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