Cetyl Alcohol → Hexadecyl Cyanoacetate

HRID 2040416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040416
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:18]([CH2:20][C:21](O)=[O:22])#[N:19].C1(N=C=NC2CCCCC2)CCCCC1.CCCCCC>ClCCl.C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[C:18]([CH2:20][C:21]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:22])#[N:19]

Komponenten

8

Edukt 4

HCID 2682Cetyl Alcohol2×HCID 8058HexaneHCID 9740Cyanoacetic acidHCID 10868Dicyclohexylcarbodiimide

Produkt 1

HCID 10049542Hexadecyl Cyanoacetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The esterification reaction of hexadecanol was carried out under an inert atmosphere (Argon). To a solution of cyanoacetic acid (7.4853 g) and of hexadecanol (10.6674 g) in 50 ml of anhydrous dichloromethane and 5 ml of ethyl acetate, 50 ml of anhydrous dichloromethane containing 9.9864 g of dicyclohexylcarbodiimide (DCC) and 50 mg of 4-(dimethylamino)pyridine (DMAP) were added. The reaction mixture was stirred for 24 hours at room temperature. Then 50 ml of anhydrous hexane were added. The formed solid residue was separated by filtration under vacuum and washed with n-hexane (70 ml). The filtrate was concentrated under reduced pressure until obtaining an amorphous yellow solid, subsequently purified by flash chromatography (ligroin/ethyl acetate 9/1 v/v), yielding 14 g of a white solid.

Aufarbeitung

  1. customThe formed solid residue was separated by filtration under vacuum
  2. washwashed with n-hexane (70 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customuntil obtaining an amorphous yellow solid
  5. customsubsequently purified by flash chromatography (ligroin/ethyl acetate 9/1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-1dbd6271138d44ce99e84b725563ac0c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580820B2

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