Ethanol → 9,10-Bis(2-chloroethoxy)-2-methylanthracene

HRID 904646

Reaktionsgleichung

Reaktionsgleichung von HRID 904646
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[OH-].[Na+].[CH2:20](O)[CH3:21].[Cl:23][CH2:24][CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O.C(Cl)[Cl:38]>[Zn]>[Cl:23][CH2:24][CH2:25][O:17][C:5]1[C:6]2[C:11]([C:12]([O:16][CH2:21][CH2:20][Cl:38])=[C:13]3[C:4]=1[CH:3]=[C:2]([CH3:1])[CH:15]=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

7

Edukt 5

HCID 702EthanolHCID 6344DichloromethaneHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 67732-MethylanthraquinoneHCID 14798Sodium Hydroxide

Produkt 1

HCID 133054499,10-Bis(2-chloroethoxy)-2-methylanthracene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

A 22.2 g. portion of 2-methylanthraquinone is reduced with 10 g. of zinc and 200 ml. of 20% sodium hydroxide in 40 ml. of ethanol, then alkylated with 50 ml. of 2-chloroethyl-p-toluene sulfonate as described in Example 1. The crude product is taken up in methylene chloride, filtered, dried over magnesium sulfate and concentrated to dryness. Recrystallization from 100 ml. of propanol gives 0.7 g. of the desired intermediate as a yellow solid, m.p. 82°-85° C.

Aufarbeitung

  1. filtrationfiltered
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness
  4. customRecrystallization from 100 ml
  5. customof propanol gives 0.7 g

Quellen und Nachweise

ORD-Eintrag
ord-a2e409b794a84f0095c4e2829b1c4c8a
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04419354

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