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Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262398
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 262398
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11]O)[OH:10])O)O)=O.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].O.[ClH:37]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[Cl:37][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6904L-(-)-SorboseHCID 57371080Sodium dodecylbenzene sulphonate

Produkt 1

HCID 741915-Chloromethylfurfural

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8154Hexadecyltrimethylammonium chloride
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a three-necked flask equipped with a condenser and a stirrer were added 2.5 g (0.014 mole) of a commercially available L-(-)-sorbose and two kinds of surface active agent, i.e., 47.1 mg (0.00014 mole) of cetyltrimethylammonium chloride and 51.3 mg (0.00014 mole) of sodium laurylbenzenesulfonate. Then, 2.5 ml of water and 15 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 30 minutes, and the mixture was stirred at room temperature for a further 2.5 hours. The reaction solution was filtered through Celite while being washed with a small amount of a water-toluene mixture. The toluene layer was neutralized, dried and concentrated to obtain about 1.0 g (theoretical yield 2.0 g) of 5-chloromethylfurfural as a crude product.

Aufarbeitung

  1. customTo a three-necked flask equipped with a condenser and a stirrer
  2. stirringthe mixture was stirred at room temperature for a further 2.5 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. washwhile being washed with a small amount of a water-toluene mixture
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b8d59b36d22144b881b29631905ac5bb
Quelldatensatz
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04154744

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