Dimethyl-2,6-naphthalenedicarboxylate → Dimethyl 1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

HRID 133120

Reaktionsgleichung

Reaktionsgleichung von HRID 133120
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17][CH3:18])=[O:16]>CC(O)=O.[Pd]>[CH2:6]1[C:5]2[C:10](=[CH:1][C:2]([C:15]([O:17][CH3:18])=[O:16])=[CH:3][CH:4]=2)[CH2:9][CH2:8][CH:7]1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

4

Edukt 1

HCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Produkt 1

HCID 11288106Dimethyl 1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of dimethyl naphthalene-2,6-dicarboxylate (25.0 g, 102 mmol) and 5% Pd—C (5.0 g) in AcOH (75 mL) was shaken under an atmosphere of hydrogen (ca. 150 p.s.i.) at 80° C. for 6 h. The reaction mixture was cooled, purged with argon, and filtered through a pad of Celite, washing with AcOH. The filtrate was concentrated under reduced pressure to give the title compound. MS: m/z=249 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. custompurged with argon
  3. filtrationfiltered through a pad of Celite
  4. washwashing with AcOH
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b476591ee8714d59a9f90638e46b9ff8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390798B2

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