Hydrochloric Acid → 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylic Acid

HRID 1285521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285521
[C:1]([C:3]1([C:14]([O:16]CC)=[O:15])[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:4]1([CH3:13])[CH3:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[C:1]([C:3]1([C:14]([OH:16])=[O:15])[CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:4]1([CH3:13])[CH3:12])#[N:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 13429895Ethyl 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylate

Produkt 1

HCID 135886061-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylic AcidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 147 mg (0.60 mmole) of cyclopropanoid cyanoester 10 (produced in accordance with Example VIII), 88 mg (0.64 mmole) of anhydrous potassium carbonate, 0.50 mL of water, and 2.0 mL of methyl alcohol was heated at reflux for 20 minutes. The product was isolated by cooling the mixture to room temperature, cautiously acidifying it by addition of 2 mL of 2M aqueous HCl, subsequent dilution with 20 mL of saturated brine, and extraction with ether. The ether extracts were washed with saturated brine, then dried over anhydrous magnesium sulfate and subsequently filtered. Removal of the ether by evaporation at reduced pressure afforded 110 mg (85% yield) of cyanoacid 18, which was immediately decarboxylated in accordance with Example XVI.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 20 minutes
  3. customThe product was isolated
  4. extractionwith 20 mL of saturated brine, and extraction with ether
  5. washThe ether extracts were washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationsubsequently filtered
  8. customRemoval of the ether
  9. customby evaporation at reduced pressure
  10. customafforded 110 mg (85% yield) of cyanoacid 18, which

Quellen und Nachweise

ORD-Eintrag
ord-642b73378b674b8ba10c1a3dc3855e2b
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567265

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