Benzyl Bromide → Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

HRID 913162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913162
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:2]1([CH2:1][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([O:20][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

Produkt 1

HCID 58012491Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylateAusbeute 109,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Benzylbromide (2.95 ml, 24.7 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (3 g, 9.87 mmol) and potassium carbonate (3.40 g, 24.7 mmol) in acetone (100 ml). The reaction mixture was refluxed for 18 hours under an atmosphere of argon. The resulting mixture was evaporated and the reaction mixture triturated with water. The resulting tan coloured solid was collected by filtration and washed with water then dried under vacuum to give the title compound (5.23 g, 10.8 mmol). LC/MS: Rt=4.13, [MH]+ 485.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe reaction mixture triturated with water
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2c45cf7241dd4a4493e02df43dc3e6d2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026270B2

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