Hydrochloric Acid → 6,12-Dioxaheptadecanenitrile

HRID 327495

Reaktionsgleichung

Reaktionsgleichung von HRID 327495
[H-].[Na+].[CH2:3]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[N:21].Cl>CN(C)C=O>[C:20](#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16][O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 141235455-Pentyloxy-1-pentanol

Produkt 1

HCID 190000196,12-Dioxaheptadecanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium hydride (60%, 0.75 g) was added to a solution of 3 g of 5-pentyloxy-l-pentanol prepared in the above-described step (1) in 50 ml of N,N-dimethylformamide. Then 2 ml of 5-bromopentanenitrile was added thereto and the mixture was stirred at 60° C. for 2 h. 3% hydrochloric acid was added to the reaction solution. After extraction with ether, the organic layer was dried and concentrated and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1) to obtain 1 g of the intended product.

Aufarbeitung

  1. extractionAfter extraction with ether
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-cf328dda49774ba882ede0a2214b8de2
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273985

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