Benzyl Chloride → HCID 14773084, Verbindung

HRID 1709133

Reaktionsgleichung

Reaktionsgleichung von HRID 1709133
[Na].[OH:2][C:3]1[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([OH:13])[CH:9]=[CH:8][CH:7]=2.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:3]([OH:2])[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 14773083Ethyl 3,5-dihydroxynaphthalene-2-carboxylate

Produkt 1

HCID 14773084HCID 14773084, VerbindungAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 7.8 g (0.34 g atom) of sodium in 1,000 cc of ethanol, was added 85 g (0.37 mole) of ethyl 3,5-dihydroxy-2-naphthoate. After one-half hour 47 g (0.37 mole) of benzyl chloride was added. The reaction mixture was warmed under reflux for 24 hours. The hot reaction mixture was filtered and cooled in an ice bath. A tan solid precipitated out, which was filtered off yielding 15.0 g (m.p. 98°-115° C.) of the crude product. Recrystallization first from ethanol and then from acetonitrile furnished ethyl 5-benzyloxy-3-hydroxy-2-naphthoate, m.p. 112° C.-114° C. in 7 percent yield (7.3 g).

Aufarbeitung

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 24 hours
  3. filtrationThe hot reaction mixture was filtered
  4. temperaturecooled in an ice bath
  5. customA tan solid precipitated out
  6. filtrationwhich was filtered off
  7. customyielding 15.0 g (m.p. 98°-115° C.) of the crude product
  8. customRecrystallization first from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bc597119003e4fbab71db07d1aa9fd87
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04948582

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