Chloroform → Hydrochloric Acid

HRID 363235

Reaktionsgleichung

Reaktionsgleichung von HRID 363235
CC1C=C(N[C:10](=[O:19])CC2C=CC(O)=CC=2)C=C(C)C=1.[OH-:20].[Na+].[C:22]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)(Cl)[Cl:30]>C1COCC1>[ClH:30].[CH:22]1([C:10]([OH:19])=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 2763537N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

Produkt 2

HCID 313Hydrochloric AcidHCID 7413Cyclohexanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5.889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% sodium bicarbonate solution. The aqueous layer on acidification with HCl yields the product 1-(4-(((3,5-dimethylphenyl)amino)carbonyl) methyl)phenoxy] cyclohexanecarboxylic acid (C23H27NO4). The product was purified by repeated extraction into ether and NaHCO3.

Aufarbeitung

  1. customTHF is removed under vacuum
  2. dissolutionthe residue is dissolved in water
  3. extractionThe precipitated solid is extracted into ether
  4. additiontreated with 6% sodium bicarbonate solution

Quellen und Nachweise

ORD-Eintrag
ord-637a7ea676094045b3fcefdd2fa06012
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872282

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