Hydrochloric Acid → 1-(1,3-Benzodioxol-5-yl)cyclobutanecarboxylic Acid

HRID 1593115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593115
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:14]#N)[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-:16].[K+].[OH2:18].Cl>C(O)CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:14]([OH:18])=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 219020081-(1,3-Benzodioxol-5-yl)cyclobutanecarbonitrile

Produkt 1

HCID 219020231-(1,3-Benzodioxol-5-yl)cyclobutanecarboxylic AcidAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

1-Benzo[1,3]dioxol-5-yl-cyclobutanecarbonitrile (1.2 g) was slurried in ethylene glycol (10 mL) in a pressure tube and a large excess of KOH (I g) was added. The tube was sealed and heated at 180° C. for 24 hours, cooled, poured into 100 mL of water, acidified with 1N HCl, extracted with ether, and the ether extracts were concentrated in vacuo and chromatographed on silica gel with an ethyl acetate:hexane:acetic acid mixture to give the desired 1-benzo[1,3]dioxol-5-yl-cyclobutanecarboxylic acid (850 mg, 65%). Data for this acid: MS 220 (M); 1H NMR (300 MHz, CDCl3): δ 11.4-11.8 (br. s, 1H), 2.78-6.85 (m, 3H), 5.95 (s, 2H) 2.75-2.85 (m, 2H), 2.40-2.55 (m, 2H), 1.8-2.2 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 182.9, 147.9, 146.7, 137.2, 119.8, 108.2, 107.5, 101.3, 52.2, 32.6, 16.7.

Aufarbeitung

  1. customThe tube was sealed
  2. temperaturecooled
  3. extractionextracted with ether
  4. concentrationthe ether extracts were concentrated in vacuo
  5. customchromatographed on silica gel with an ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-55a82e5d6b794b1998c5565f0715289b
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294637B2

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