Ethylene Glycol → 3',4'-Dihydro-2'-(1H-1,2,4-Triazol-1-yl)-Spiro-[1,3-Dioxolane-2,1'(2'H)-Naphthalene]

HRID 2165989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165989
[N:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH:5]=[N:4][CH:3]=[N:2]1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>ClCCl.C(O)CCC>[N:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]32[O:19][CH2:18][CH2:17][O:16]3)[CH:5]=[N:4][CH:3]=[N:2]1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 146988003,4-Dihydro-2-(1H-1,2,4-triazole-1-yl)1(2H)-Naphthalenone

Produkt 1

HCID 197619943',4'-Dihydro-2'-(1H-1,2,4-Triazol-1-yl)-Spiro-[1,3-Dioxolane-2,1'(2'H)-Naphthalene]

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 10 g. 3,4-dihydro-2-(1H-1,2,4-triazol-1-yl)-1-(2H)-naphthalenone, 5.8 g. ethylene glycol and 11.5 g. p-toluenesulfonic acid was refluxed in a mixed solvent of 150 ml. toluene and 70 ml. n-butanol under a Dean-Stark [trademark] trap for 48 hours. The solvent was evaporated leaving a slurry which was taken up in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The extract was dried in sodium sulfate, filtered and evaporated leaving an oily residue which crystallized on cooling to yield 1.5 g. of white crystals. These white crystals were 3',4'-dihydro-2'-(1H-1,2,4-triazole-1-yl)-spiro-[1,3-dioxolane-2,1'(2'H)-naphthalene. This compound had a melting point of 108° C.

Aufarbeitung

  1. additionA mixture of 10 g
  2. customThe solvent was evaporated
  3. customleaving a slurry which
  4. washwashed twice with 10% aqueous sodium hydroxide and once with water
  5. dry with materialThe extract was dried in sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customleaving an oily residue which
  9. customcrystallized
  10. temperatureon cooling
  11. customto yield 1.5 g

Quellen und Nachweise

ORD-Eintrag
ord-48027628fa7447ea9860ebb15c41398f
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04943311

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