Benzene, 1,3-bis(chloromethyl)- → 1,3-Bis(6-carbomethoxy-2-naphthoxymethyl)benzene

HRID 329998

Reaktionsgleichung

Reaktionsgleichung von HRID 329998
[Na].[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([OH:16])[CH:10]=[CH:9]2)=[O:5].[C:17]1([CH2:25]Cl)[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Cl)[CH:18]=1>CN(C)C=O>[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([O:16][CH2:25][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:16][C:11]3[CH:10]=[CH:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=4)[CH:12]=3)[CH:18]=1)[CH:10]=[CH:9]2)([O:3][CH3:2])=[O:5]

Komponenten

5

Edukt 3

HCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 390995Methyl 6-hydroxy-2-naphthoateHCID 5360545Sodium

Produkt 1

HCID 143236721,3-Bis(6-carbomethoxy-2-naphthoxymethyl)benzeneAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To sodium salt of 2-hydroxynaphthalene-6-carboxylic acid methyl ester (44.8 g) N,N-dimethylformamide (200 ml) was added with stirring at room temperature. Then a solution of m-xylylenedichloride (17.5 g, 0.1 mol) in N,N-dimethylformamide was added in drops thereto in 10 minutes. The reaction mixture was stirred at 105° C. for 4 hours and then cooled to give a precipitate. The precipitate was rinsed with N,N-dimethylformamide, treated with hot water at 80° C. for 30 minutes with stirring, and then with methanol at 60° C. for 30 minutes with stirring; cooled, filtered and dried to give a white crystals of 1,3-bis(6-carbomethoxy-2-naphthoxymethyl)benzene (39.7 g, yield 77.8%): m.p. 177.3°-178.0° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 105° C. for 4 hours
  2. temperaturecooled
  3. customto give a precipitate
  4. washThe precipitate was rinsed with N,N-dimethylformamide
  5. additiontreated with hot water at 80° C. for 30 minutes
  6. stirringwith stirring
  7. stirringwith methanol at 60° C. for 30 minutes with stirring
  8. temperaturecooled
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-22f39fed4e454e658fd48847d8d97225
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894359

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