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Hydrochloric Acid → 3-(2-oxocyclododecyl)propanoic acid

HRID 2083442
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2083442
C(O[C:4]([CH:6]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:18])=O)C.[H-].[Na+].[C:21]1(=[O:25])[O:24]C[CH2:22]1.[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[O:18]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:6]1[CH2:4][CH2:22][C:21]([OH:25])=[O:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 2365Beta-PropiolactoneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 4463978Cyclododecanecarboxylic acid, 2-oxo-, ethyl ester

Produkt 1

HCID 27750833-(2-oxocyclododecyl)propanoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Cyclododecanone and diethyl carbonate were allowed to react in the presence of a base to give 2-ethoxycarbonylcyclododecanone in 93% yield. Ten grams of the 2-ethoxycarbonylcyclododecanone was dissolved in 40 ml of toluene and the resulting solution was added dropwise into a solution of 2.4 g of sodium hydride (purity 60%) suspended in toluene and kept at 80° C. After the completion of the dropping, the solution thus obtained was stirred for 30 minutes and then the reaction temperature was cooled to room temperature. Thereafter, into the solution was dropped 5.7 g of β-propiolactone and further 25 ml of aqueous sodium hydroxide solution was added, and was refluxed for 4 hour. After the reaction was complete, the aqueous layer of the solution was drawn off and acidified with hydrochloric acid to give 8.5 g of β-(2-oxocyclododecyl)propionic acid as white crystals. The product melts at 101° to 102° C.

Aufarbeitung

  1. customkept at 80° C
  2. customAfter the completion of the dropping, the solution thus obtained
  3. additionwas added
  4. temperaturewas refluxed for 4 hour

Quellen und Nachweise

ORD-Eintrag
ord-0c627b1fa6a845b8af6230dae83cdf31
Quelldatensatz
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04085274

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