Formic Acid → 1,2,2,4-Tetramethyl decahydroquinoline

HRID 2285994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2285994
[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.[CH:14](O)=O.C=O.[OH-].[Na+]>O.C(OCC)C>[CH3:14][N:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:10]([CH3:12])[CH2:11][C:2]1([CH3:13])[CH3:1]

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 226287862,2,4-Trimethyldecahydroquinoline

Produkt 1

HCID 205430951,2,2,4-Tetramethyl decahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1,2,2,4-tetramethyl decahydroquinoline was prepared. 36.3 grams (0.2 mole) of 2,2,4-trimethyl decahydroquinoline of about 58% cis structure was placed in a reactor vessel equipped for agitation. Formic acid, 20.2 grams (0.44 mole) was added dropwise to the reactor vessel followed by the slow addition of 17.4 grams of 38% by weight formaldehyde in water solution. After addition, the mix was refluxed at for 4 hours. A 5 N sodium hydroxide solution was then added until the mix was basic. Diethyl ether was added and the mix separated out and the ether fraction obtained. The fraction was concentrated and then distilled using a 3" Vigreaux column to yield 5.4 grams of a product boiling at 70° C. at 0.6 mm Hg. The NMR spectra of the product was consistent with the desired product, 1,2,2,4-tetramethyl decahydroquinoline. The theoretical carbon, hydrogen, nitrogen analysis for the formula C13H25N is 79.92% carbon, 12.90% hydrogen, and 7.17% nitrogen while measured values were 77.23% carbon, 13.13% hydrogen, and 6.56% nitrogen.

Aufarbeitung

  1. customwas placed in a reactor vessel
  2. customequipped for agitation
  3. additionAfter addition
  4. temperaturethe mix was refluxed at for 4 hours
  5. customthe mix separated out
  6. customthe ether fraction obtained
  7. concentrationThe fraction was concentrated
  8. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-edeb6116794e4ab38eb8e5e07e54f9a7
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04326061

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